Having traveled through the entire New England region for 15+ years, I’ve been able to get a strong understanding on the best things to do, and I’m so thrilled that I’ve finally developed my ultimate 7 Day New England Itinerary to share with you!
A 7-day itinerary to tour New England has been one of my most requested topics, and I totally understand why. It’s so hard to look at a region comprised of 6 gorgeous states, and try to figure out what’s worth your time, and what you can leave out. Well, good news – I’m taking the guess work out for you. In all my years of traveling through this region, I’ve cherry-picked what I think is the best route to take to plan the perfect road trip in 7 days.
While I think everything is pretty much worth your time in New England (I’m a bit biased!), this itinerary focuses on the best of the best, and also takes into consideration efficiency so you have as much time as possible to also enjoy your destinations.
This itinerary is also geared toward those who are visiting New England for the first time. With that, let’s get into it, shall we?
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How Many Days Do You Need In New England?
You can easily spend anywhere from a few days to a month in New England, so this entirely depends on how much time you really have to dedicate to your trip. This post will prove that you can easily see some of the best things in this region with my 7 Day New England road trip itinerary.
But, that said, more is always more when it comes to time to travel, right? 😉 So of course, you can easily turn this itinerary into a 10-day adventure, or even two weeks. Under my 10 Day New England road trip itinerary option later in the post, you’ll see that I’ve made notes on side excursions where you can easily add in a day or two to extend your trip even further.
And of course, you can definitely see some of the best places in just 5 days, and I’ve included a 5-Day option at the very end for those who don’t have as much time (and don’t worry, it’s still pretty great!).
My motto is always, “Even if I just have one day, it’s better than not going at all,” so whatever time you have for your trip with definitely be worth it. I’m excited to cheer you on as you plan your trip 😊
Where To Start A 7 Day New England Road Trip Itinerary?
For any road trip through this region, Boston is the best place to start, especially if you’re flying in. Boston Logan International Airport typically offers the cheapest flights to this area, and is also a worthy destination to explore on its own.
Not only that, this city also incredibly convenient to most places in New England, and is centrally-located in the region, and therefore, is just the easiest starting point. For that reason, pretty much all of my itineraries on this website start in Boston because after years of experience, I’ve found this to be the absolute best option.
If you’re not flying in, however, and already live in this area, or are driving in from nearby, Boston is still a great starting point (especially if you’ve never been!). But you can definitely adjust this itinerary to start from anywhere in New England that best suits your needs.
The only time I would suggest using a place like Portland, Maine as your starting point if if you plan to really only explore the northern areas of New England, like the rest of Maine or New Hampshire. But even in that case, Boston is still just as convenient, so it will then simply depend on personal preference at that point.
7 Day New England Road Trip Overview
Day 1: Boston – New England’s biggest and most exciting city!
Day 2: Woodstock – Vermont’s most beautiful town.
Day 2 Alternative Option: Skip Woodstock, and stay an extra day in Boston, with a day trip to Salem if you’d like.
Day 3: The White Mountains in New Hampshire – Home to breathtaking mountain views, and New England’s highest peak.
Days 4-5: Bar Harbor and Acadia National Park – One of the most charming coastal towns in New England, and the spectacular views in the park make this destination worthy of two nights.
Day 6: Drive to Portland, Maine, with optional stops along the way.
Day 6 Alternative Option: Stay the night in a smaller coastal town if that’s more your speed!
Day 7: Head back to Boston, with some great stops along the way.
Notes About This Itinerary
→ For some stops along this route, I also suggest other options to really help you create the ultimate road trip for you based on your preferences. So keep an eye out for those, and get ready to take some notes!
→ This 7 Day New England road trip itinerary also follows a true road trip style, meaning you’ll be in a different town each night of your stay (with one exception, which is Bar Harbor). You can certainly tweak that to your liking if you prefer to stay in one place for two or more nights – do what feels right for you.
→ Lastly, this itinerary was intended to show you around all the different landscapes New England has to offer, so I wanted to include a mix of urban, countryside, mountains and coastal to show you the very best of it all. I also focused on locations that are largely perfect to visit year-round, so seasonality was not factored in.
Day 1: Boston
Boston is one of my all-time favorite cities, and as mentioned, it’s the absolute best place to start your road trip – especially if you’re flying in. I love that it feels like an exciting city, but is also incredibly charming, historic and packed with character. There’s just something very cozy about it, and it’s most definitely worth spending a day exploring during your 7 day New England road trip.
An alternative option, depending on how tired you’ll be once you arrive, is to tack Boston on at the very end. In this case, you’ll want to immediately depart for Woodstock once you arrive, and then spend your last day in Boston (but follow this itinerary for everything else in order).
Here are some awesome things to consider doing on your day in Boston:
- Walk the Freedom Trail: this group tour is an excellent choice!
- Meander through my two favorite neighborhoods: Beacon Hill & the North End.
- Stroll along the waterfront areas – the Charles Esplanade is especially beautiful.
- Walk through the Public Gardens – the bridge is such a great spot for gorgeous photos.
- Eat, eat, and then eat some more. The culinary scene in Boston is incredible, and seafood here is a specialty.
- In fact, take a food tour for the inside scoop on all the best places: here are my favorite food tours in Boston.
- Grab some cannoli at Mike’s Pastry.
Hotel suggestions in Boston:
Splurge: Boston Harbor Hotel. A 5-star waterfront hotel that’s more than worth the splurge to kick start your amazing road trip through New England. The location is also convenient to a lot of attractions.
Moderate: Revere Hotel Boston Common. I stay here a lot when I visit Boston. It’s a great location that’s walkable to a lot.
Budget: HI Boston Hostel. Boston is typically an expensive city to visit unless you’re coming in the winter, and this hostel is a great option to save some money during your stay. It also has an awesome location.
Day 2: Woodstock, Vermont (2h 15m From Boston)
Why Woodstock Next? No trip to New England is complete without a stop in a charming Vermont town, and Woodstock is the best of the best when it comes to idyllic scenery and character. It’s also home to “Vermont’s most beautiful address,” which I’ll tell you about under the suggestions on where to stay.
Woodstock has a wonderful town center, where you’ll find independent shops, cafés, and restaurants, covered bridges, farms, and it’s also surrounded by beautiful rural scenery once you drive outside of town. It’s the perfect option for this itinerary if you’re hoping to get a glimpse of Vermont.
Here are some awesome things to do in Woodstock, VT:
- Meander through the most adorable village where all the shops and restaurants are. This part of town is entirely walkable, so park and enjoy!
- Visit the three covered bridges: Middle, Taftsville and Lincoln.
- Explore Billings Farm & Museum.
- Taste local maple syrups and cheeses at Sugarbush Farms.
- Take a drive to Farmhouse Pottery, just outside of the town center, which is now a famous ceramics shop – they have a studio on-site where you can watch artisans at work, or you can book a pottery session with them!
Psst! I have an entire post all about the best things to do in Woodstock, VT, if you’d like more ideas and info 😉
Where to stay in Woodstock, VT:
Luxury option: Woodstock Inn & Resort (Vermont’s most beautiful address!). It’s a splurge, but located right in town, and the perfect way to treat yourself for a 1 night stay.
Moderate: 506 On The River Inn. Very beautiful hotel that’s right on the river and feels cozy.
Budget: The Vesper. A cute little B&B with modern rooms, great prices, and walkable to the village.
Insider Tips: Woodstock tends to be an expensive place to visit, so if you’re on a budget, the nearby town of Quechee is a great alternative, and is only about 15 minutes from Woodstock. Quechee is also very cute and I love visiting both towns when I’m in the area.
Also, if you visit in the fall during foliage, or your stay happens to be on a weekend, some of these hotels may have a 2-night minimum stay requirement, so keep that in mind.
Alternative Option: If you would prefer to spend 2 nights in Boston and skip Woodstock, you can most definitely do that. Boston is a great place for day trips to other nearby areas, including Provincetown on Cape Cod, as well as Salem. A ferry will take you from Boston to Provincetown, and to Salem, so you still won’t need to pick-up your rental car right away if you choose this option. These ferry options are seasonal, so plan accordingly.
→ Click here to check out ferries from Boston to Provincetown
→ Click here to check out ferries from Boston to Salem
Psst! I have some helpful guides including planning the perfect Salem, MA day trip, and the best time to visit Salem if you need more information 😉
Day 3: The White Mountains, New Hampshire (1h 30m From Woodstock)
Why White Mountains Next? They’re on the way to Acadia National Park (which is the next stop!), and they’re very worth your time (especially if you’re traveling in the fall season). The White Mountains are home to a great mix of cute towns, epic mountain views, and amazing parks or hiking and scenic drives.
While the White Mountains doesn’t necessarily offer that New England charm you’re probably expecting, I still think this region is worth visiting on your way to Acadia for the reasons mentioned above. The drives through the White Mountains National Forest, and Crawford Notch State Park is so beautiful, and offer such a well-rounded perspective of New England’s beauty, when you combine this region with all the other coastal stops on the rest of this itinerary 😉
Here are some awesome things to do in the White Mountains:
- Explore Franconia Notch State Park, and with 1 day, I suggest prioritizing Flume Gorge, which is perfect for all ages, and one of the most popular attractions in the entire state that’s worth your time.
- If you’re looking for a fun hike, the Artist Bluff Trail offers incredible views of Echo Lake.
- Ride the Cannon Mountain Aerial Tramway to the mountain’s summit for awesome views.
- Explore The Basin, which is very close to Flume Gorge, and is very quick and easy.
Where to stay in the White Mountains? I highly suggest Littleton. It’s a charming little town with awesome shops and restaurants (it’s often regarded as having one of the best Main Streets in the U.S.!), and it’s also very close to some of the top must-see things from my list above, making it super convenient and efficient for 1 day.
However, I have an entire detailed post on where to stay in the White Mountains, if you’re looking for more of a breakdown of the towns, and my hotel suggestions.
Hotel suggestions in Littleton:
Thayers Inn: Located right on Main Street in the heart of downtown, and very cozy. Keep in mind that this is a historic hotel, so they’re not able to make a lot of modern updates, so it’s not for everyone – but I really enjoyed my stay here and appreciated how it felt like I was stepping back in time!
Hampton Inn: A nice option that’s on the commercial side of town, but very close to the highway to get around quicker.
Pro Tip: You’ll drive right past Hanover, NH on your way from Woodstock, which is home to Dartmouth College, and is a really adorable little town to stop in for lunch, or to take a driving break. Right in the same area is Norwich, VT, which is home to the King Arthur Baking Company campus, and is a really fun spot to pick up some baked goods (especially breads and pastries!) and also have lunch outside on their lawn.
Here are some posts you may find helpful while you plan your time in the White Mountains:
- Things To Do In Franconia, NH
- Things To Do In Littleton, NH
- Things To Do In Lincoln, NH
Days 4-5: Acadia National Park & Bar Harbor (4h 30m From The White Mountains)
Why Acadia National Park & Bar Harbor Next? Acadia is one of the most incredible and iconic destinations in the Northeast, and definitely one of the best places to visit in New England. Even though it’s pretty far north, it’s so worth it for the stunning views. I’ve budgeted two nights here because your drive from the White Mountains to Acadia is a bit longer, and because Acadia just warrants extra time.
Also, Bar Harbor, I think, it’s such a quintessential coastal New England town filled with character. The town is small, and very walkable, and you’ll get some nice views of the bay and harbor just by walking along the town’s waterfront.
There’s also opportunities for boat tours from town, great restaurants to choose from, and of course, quick access to Acadia!
Here are some awesome things to do in Acadia National Park for a short trip:
→ Walk Ocean Path, which connects Sand Beach to the Otter Cliffs. This is the perfect scenic walk to tackle with a short amount of time because it’s easy, and offers some of the best and most iconic views of the coastline.
→ Thunder Hole is along Ocean Path, so you’ll pass right by it if you walk this trail. If you’re there on a windy day, the waves will crash so loudly that it sounds like thunder. Otherwise, it’s just a scenic overlook that’s still worth a stop.
→ If you’d like to tackle a hike, a nice one for a quick visit to the park is Great Head. This starts at Sand Beach, and is pretty easy (with some rock scrambling at the beginning), but offers incredible views along the way). After this, you can walk back across Sand Beach and do the Ocean Path for the perfect day in Acadia.
→ Lunch at the Jordan Pond Restaurant is also really fun, and a more relaxing way to spend some of your time in the park. It’s open seasonally only, so plan accordingly, and is famous for their popovers, and incredible views of the famous Bubble Rocks.
→ Sunrise at Cadillac Mountain is one of the most popular things to do, and definitely worth your time! This location is one of the first places in the U.S. to watch the sunrise, and it’s the actually first sunrise spot between October 7 through mid-March. This is another great reason to spend two nights here. Note: Reservations are now required when taking the auto road to Cadillac Mountain’s summit mid-May through October. Click here for more info!
→ Cover more ground by renting E-bikes to explore the park!
→ Click here for more info on renting E-bikes for your trip to Acadia
Psst! I have a few posts on Acadia that you may find helpful, including:
- My Perfect Acadia National Park Itinerary
- The Best Time To Visit Acadia National Park
Where to stay while visiting Acadia National Park? Bar Harbor! This lovely little coastal town is the gateway to Acadia, and where most people stay when exploring the park. This is another reason why I’ve given you two days because Bar Harbor is also a worthy town to explore on its town.
Hotel Suggestions in Bar Harbor:
Bar Harbor Inn & Spa: Located right on the waterfront in town, it’s a great place to stay for walkability to town, and if you’re looking for the best amenities and a nicer place to stay.
Bar Harbor Villager Motel: An awesome motel in the center of Bar Harbor’s village, with spacious and updated rooms, and walkable to everywhere in town. I like to stay here when I plan to spend most of my time hiking in the park, and just need a cozy place to crash at night.
Pro Tip: When driving from Littleton to Acadia, I suggest driving to Lincoln, NH first, and then taking Route 112 to Conway, which is the famous Kancamagus Scenic Highway. This drive takes you through the heart of the White Mountains with some really nice overlooks to stop at, and only adds 30 extra minutes to your drive (plus extra time for any stops you make).
Pro Tip: The Kancamagus Scenic Highway does not have bathrooms, gas stations or cell service, so plan accordingly!
Day 6: Portland, Maine (3h From Bar Harbor)
Why Portland Next? Not only is Portland a very cool city with lots of history and an awesome culinary scene, it’s also on the drive back toward Boston. Portland has a great mix of urban vibes and authentic fishing port scenery, so it offers the best of both worlds, too.
Here are some awesome things to do in Portland:
→ See all 3 of Portland’s lighthouses. If you only have time for one, however, make it Portland Head Lighthouse. This is one of the best lighthouses in New England, and definitely worth your time! But keep in mind that the other two lighthouses (Bug Light and Spring Point Ledge Light) are a very short drive away, so it’s easy to see all three in a few hours at most.
→ Take a tour! This culinary walking tour of the city is a great way to enjoy the best food, and this tall ships cruise around the bay is an awesome scenic option to get the most out of your visit.
→ Go beer tasting. Portland is home to some of the best breweries in New England, and the city has tons of them. I have an entire guide on my favorite breweries in Portland, Maine, if you’d like some suggestions 😉
→ Wander through Old Port, the most historic and charming part of the city.
Hotel Suggestions in Portland:
Splurge: The Press Hotel. It’s right on the water and in the center of Old Port, making this an awesome hotel to splurge on for a fancier stay in Portland.
Moderate: Cambria Hotel. Also in the Old Port district, this lovely hotel has modern rooms and a great location.
Budget: Black Elephant Hostel. Portland tends to be a pricey city to visit, and even though this is the only hostel in the city, it’s incredibly well-regarded, and will be significantly less expensive than a hotel.
Pro Tip: If you would rather spend your first day in Portland exploring the city, you can do the lighthouses the next morning on your way back to Boston. The lighthouses are located outside of the city’s downtown in South Portland, which you’ll pass through on your drive to Boston.
Optional stop to make on the drive: There are some wonderful towns to explore on the drive from Bar Harbor to Portland, and I detail my favorites to suggest in my guide on driving from Portland, Maine to Acadia National Park. Many of these stops will add extra time to your drive, but depending on your road trip style, they may be worth it for you!
Day 6: Alternative Option: Stay In A Smaller Coastal Town Instead
If staying in a city isn’t exactly your speed, and your goal is to visit more of the smaller towns along the coastal, well I’ve got you covered. And honestly, that’s usually my preference, too 😉 While I love Portland, and think there’s some very cool things to see there, one of the best parts of New England is the charming smaller towns to explore.
My favorites to suggest for this road trip are: Boothbay Harbor, Kennebunkport, and Ogunquit.
Boothbay Harbor is a wonderful, charming little town on the water, and has a more fishing village vibe to it. Lots of awesome boat tours depart from here, too.
Kennebunkport perfect encapsulated New England coastal beauty with a wonderful town center called Dock Square, and beautiful coastline near the beaches and on Cape Porpoise.
Ogunquit is also very idyllic, and is known for having one of the best beaches in New England. I love the walkable downtown that’s also walkable to the beach. Ogunquit also has one of my favorite things to do in all of New England: the Marginal Way coastal walk.
All of these places will make a great place to spend a night on this road trip if you’d prefer a small coastal town over staying in a city like Portland.
Psst! I have detailed guides that may help you decide, which are the best things to do in Boothbay Harbor, and the best things to do in Ogunquit.
Day 7: Back To Boston With Stops Along The North Shore (2h Without Stops)
Why The North Shore Next? As you make your way back to Boston, you’ll drive down the Massachusetts North Shore, which is packed with gorgeous and charming little coastal New England towns. These towns are all pretty close to another, too, which makes it easy to stop in quite a few during your drive. These towns are actually some of my favorites in all of New England.
Here are some more towns you can choose to stop in on your drive back to Boston:
→ Portsmouth, NH – while not technically part of the North Shore, it’s along the route, and a very beautiful coastal city with awesome shopping and restaurants.
→ Newburyport, MA – Some of the best shopping in New England can be found here in Market Square and Tannery Marketplace. It’s also home to Plum Island.
→ Rockport, MA – One of my all-time favorite coastal towns because it’s so unique and loaded with character. This one is a bit of a detour off the main route, but not by much (and worth it, in my opinion).
→ Salem, MA – Most known for its Halloween celebrations, but is a very beautiful and charming city that’s awesome year-round.
→ Marblehead, MA – An underrated town that’s very beautiful and historic, and loaded with gorgeous coastline.
Where you choose to stop will largely depend on how much time you have, and I honestly think they’re all worth your time! Of them all, I think I prefer Rockport the most, as I think it has the most unique scenery,, but you can’t go wrong with any of the places I mentioned above. I’ve been to them all, and continue to visit them all regularly 😉
Here are some posts that will help you plan your drive down the North Shore:
- Best Things To Do On Cape Anne (part of the North Shore)
- Best Things To Do In Marblehead, MA
- Best Things To Do In Rockport, MA
- Best Stops To Make Driving Boston To Portland, Maine
Alternative option: If you didn’t stop in Ogunquit or Kennebunkport the night before, these two coastal towns are also worthy of your time!
10 Day New England Road Trip Itinerary
With 10 days for your New England road trip, we can pack even more exciting places to visit into your itinerary!
I’ve broken down this 10 Day New England road trip itinerary for you below, and since many of the same stops are included, I’ve done a more abbreviated version. You’ll want to refer to the above 7 Day Itinerary for all the important information. But don’t worry! I’ve included all my pro tips for the new additions to this option, too.
Days 1-2: Boston, with an optional day trip to Salem, Provincetown or a whale watch tour from Boston’s Harbor. Since you have the extra day, I suggest taking a day trip to one of these 3 destinations, but if you would prefer to relax and explore the city even more, you can do that, too.
Day 3: Newport, RI.
Why Newport, RI Next? It’s only 1 hour and 30 minutes from Boston, and such a beautiful coastal town to visit in New England. Because of its location, it makes it easy to squeeze into a 10-day New England itinerary, too.
Here are some suggestions of awesome things to do in Newport, RI:
- Explore Cliff Walk.
- Tour the stunning Gilded Age mansions.
- Have lunch at Cliff House.
- Take this awesome morning mimosa boat tour in Newport!
- Explore the city by trolley, which includes The Breakers mansion!
Psst! I have a detailed guide on the a Newport, RI day trip, which is helpful for 1-night stays, too 😉
Newport, RI hotel suggestions:
Splurge: The Cliffside Inn, which is walkable to Castle Hill Lighthouse, pictured above!
Moderate: Mill Street Inn, which is in a historic building that’s walkable to a lot of places downtown, including the waterfront. They also have a great rooftop patio!
Day 4: Woodstock, VT
Days 5: White Mountains, New Hampshire
Day 6-7: Acadia National Park & Bar Harbor
Day 8: Boothbay Harbor, ME
Why Boothbay Harbor Next? As mentioned, one of my favorite little coastal towns in Maine is Boothbay Harbor because it’s loaded with charm and character, and offers so many incredible opportunities to get out onto the water with boat tours. Of all the places you can stop at on your way from Acadia to Portland, this is one of my favorites.
Here are some wonderful things to do in Boothbay Harbor:
- Take this awesome boat cruise to see seals, lighthouses and a lobster haul tour!
- Stroll through the adorable downtown area.
- Take in the views from the footbridge.
- Have a delicious lobster roll at Shannon’s Unshelled.
Hotel Suggestion in Boothbay Harbor:
The Harborage Inn on the Oceanfront is my favorite place to stay in Boothbay Harbor. The location is perfect and walkable to town, but set back enough so that it’s very peaceful. If you can, splurge on Room 8 for panorama views of the water (it seriously feels like you’re floating on water).
Day 9: Portland, ME
Day 10: Back to Boston, making stops along the North Shore on the way.
Alternative suggestion: If you wanted to skip Woodstock, VT for this option, you could add an extra day in the White Mountains. You could also skip Woodstock and add a night in the North Shore on your drive back to Boston. For this option, I would suggest Newburyport.
Do I still think Woodstock, VT is worth the excursion? Yes! But an extra day in the White Mountains or a night in the North Shore may appeal more to some of you, too. Do what fits your preferences the most 😊
I love Newburyport because it’s a wonderful balance between charming coastal town and historic shopping village. It pretty has much something for everyone, including a beautiful waterfront park, the nearby Plum Island for beaches and nature trails, and some of the best shopping in New England. For this particular itinerary, I think it’s a great option because it’s also the furthest north, and will break up your trip nicely.
Here are some fun things to do in Newburyport:
- Induldge in some retail therapy in Market Square and Tannery Marketplace.
- Walk the path in the Waterfront Park.
- Explore Maudslay State Park.
- Drive to Plum Island to see the beaches and the nature trails at Parker River NationalWildlifeRefuge.
Newburyport hotel suggestion:
Compass Rose Inn is the best place to stay in Newburyport and feels like a big, warm hug when you arrive. In a beautiful and historic home, and each room is a suite with a fireplace. It’s also walkable to town, and a complimentary breakfast is included.
5 Day New England Road Trip Itinerary
Don’t have 7 or 10 days for a New England road trip? No problem! Having put a lot of thought into the best 5 Day New England itinerary, you can easily make this a jam-packed road trip style trip, or a more relaxing getaway that allows you additional time at each destination, but doesn’t get to as many places. Not sure which is right for you? I’ve outlined both to help you decide.
As before, refer to the first 7 Day New England road trip itinerary option for more detailed information on each destination.
5 Day Road Trip Itinerary From Boston
Day 1: Boston
Day 2: The White Mountains, New Hampshire
Day 3-4: Acadia National Park
Day 5: Drive back to Boston, stopping at the Portland Lighthouses, and 1-2 towns along the North Shore region on your way.
5 Day Relaxed Itinerary From Boston
Days 1-2: Boston. Two days will allow you to settle in and enjoy a more relaxed pace.
Pro Tip: If you’re not flying into Boston (ie, you’re driving in), you don’t have to stay right in Boston. You can definitely stay in a cute nearby town like Salem or Gloucester, and then take a day trip to Boston for a more relaxing getaway.
Days 3-4: Newport, RI & Mystic, CT. From Newport, Mystic, CT is only about a 1-hour drive, which makes this an easy and relaxing afternoon excursion that’s stress-free.
Psst! I have a detailed guide on the best things to do in Mystic, CT, if you need more ideas 😉
Day 5: Back to Boston, with stops in either Plymouth and Scituate on the way back (or both!). These two towns are south of Boston, and more convenient to visit when driving from Newport. I love them both, and they offer lots of charm, shopping, dining and beautiful sites to see. Of the two, Scituate is smaller with fewer things to do, but very beautiful.
Alternative suggestion 1: Stay right in Boston for all 5 days, and take day trips! Since Boston is in such a great area, it’s very easy to get around. And as mentioned before, you can take a ferry to Provincetown on Cape Cod, or over to Salem, and you won’t need a car for either of these two excursions.
Alternative suggestion 2: Stay in Boston for 2-3 nights, and spend 2-3 nights on Cape Cod with a day trip to one of the islands (Nantucket or Martha’s Vineyard). This option will be very coastal, and provides you with some of the best beaches and coastal towns in Massachusetts.
Here are some posts that may help you if you like this option:
- Best Towns To Stay In On Cape Cod
- Best Things To Do In Provincetown, MA
- Cape Cod Day Trip Guide
- Martha’s Vineyard Day Trip Guide
- Nantucket Day Trip Guide
- Is Nantucket Or Martha’s Vineyard Better For A Day Trip?
- How To See Martha’s Vineyard Without A Car
Alternative suggestion 3: Stay in Boston for 2 nights, and then drive to the North Shore for 2 nights, and then maybe Portland for 1 night. Just north of Boston, the North Shore region includes Salem, Marblehead, Manchester-By-The-Sea, Gloucester, Rockport, Essex and Newburyport. All of these towns are pretty close to another another, and it would be easy to pick one to stay in, and take afternoon trips to the others.
Portland is also within 1 hour and 30 minute at the most from these towns, making it easy to pop over for the day, or a night.
Best Way To Get Around New England
The best way to see New England is definitely by car. If you fly in, I suggest renting a car from the airport to begin your road trip. If you plan to spend a day or two in Boston before beginning the road trip, I would say to hold off on renting your car until you’re ready to leave Boston.
Boston has an awesome public transit system, and Uber and Lyft are readily available, so a car will be more of a hassle to park in the city.
What To Pack For A New England Road Trip
This will, of course, depend on entirely on the time of year you visit, as New England is a four-season climate. I always suggest checking the weather reports a few days before leaving to get a more accurate idea of what the weather and temperatures will be like.
I love to remind people that New England can be moody and weather can change frequently. Even in the summer, you could have chilly days, and in the winter, you might experience a warm day. Although, generally speaking, you’ll find it’s pretty much what you would expect of a four-season climate: A wet and rainy spring, a warm or hot summer, a chilly fall, and cold and snowy winter.
Here are a few suggestions and tips on packing for a New England road trip that you not have thought of:
→ A reusable water bottle to reduce single-use plastic.
→ Dramamine if you plan to do any boat tours, and you’re prone to seasickness.
→ Day pack for essentials like your water bottle, camera, sunscreen, etc.
→ Comfortable shoes for exploring towns. Keep in mind that places like Boston, Nantucket, and historic small towns often have uneven cobblestone or brick streets.
→ Hiking boots if you plan on doing any hikes.
→ In general, plan to keep your clothes fairly casual. New England can be fancy if you plan a special dinner out, but is overall pretty casual. Take a look at your specific plans and eliminate any extra fancy outfits that you likely won’t need. You probably won’t need any if you don’t plan to dine out anywhere upscale.
→ Light jackets or sweaters for mornings and evenings (even in the summer!).
→ Waterproof jacket and boots if you plan to visit in the spring or fall.
→ Don’t forget your camera! You may also want to consider an iPhone tripod with a remote shutter to elevate your travel photos from selfies to wall-worthy shots. This one on Amazon is inexpensive and perfect for the average traveler!
New England Road Trip FAQ
Is New England Easy To Drive Around?
Very! Of course, you’ll experience traffic when you’re close to, or in, a city like Boston or Portland. In that case, it’s just like driving in any other city. But overall, New England is very easy to drive around.
One thing I like to remind people is that in the more rural places, you will likely drive on a lot of dirt roads, so just be careful of any pot holes and go slowly, especially in Vermont and New Hampshire.
Is It Safe To Take A Winter New England Road Trip?
Yes! As long as you’re comfortable driving in the snow, you’ll be totally fine. Chances are, if you’re visiting in the winter, you’re excited to check out places like New Hampshire or Vermont, and those two states are among the top 3 snowiest in the whole country. So, just know that you will experience snow, and you’ll definitely be driving in it.
But generally speaking, most places are great at plowing roads, so unless you happen to visit during one of our big nor’easter storms, driving is easy. Just practice normal precautions, and don’t drive if the snow is coming down really hard.
I have an entire guide on all my favorite New England winter getaways, if you’re looking for the best winter destinations in this region.
Is Cell Service Reliable All Over New England?
Yes and no, and it depends on where you’re going. For the most part, cell service is completely reliable, and Google Maps will be able to take you everywhere.
However, in more remote places, again like in Vermont or New Hampshire, or even along the coast at some lighthouses or in Acadia, you will lose cell service more than you think! I highly recommend offlining maps for your entire route just to be safe. I can’t tell you how many times I’ve lost service while driving in VT and NH and didn’t offline maps, only to very much regret it in the moment!
Why Is Connecticut Not Part Of Your Itineraries?
I love Connecticut! But the hard thing about it is its location. It’s so far southwest, in the exact opposite direction of Acadia National Park, and most of the other top destinations to visit. And since Acadia is one of the most amazing New England locations that everyone should see when they visit, I had to exclude Connecticut from the itinerary options only for the sake of time. I personally think Acadia, and the other places I’ve mentioned, offer much higher payoff for your driving time than destinations around Connecticut.
That’s why I was only able to squeeze in a quick afternoon trip to Mystic, CT in the 5-day option.
What About A Fall Foliage Road Trip?
I’ve got you covered! I have an entire post on the perfect New England fall road trip, which is one I’ve perfected over many years of exploring this region in the fall season. This road trip makes stops in similar places, but has more of a focus on the best places for foliage.
You May Also Enjoy Reading:
- Best Things To Do In New England
- Best Time To Visit New England
- Best Boston Hotels Near The Aquarium
- Best Christmas Towns in New England
- Best New England Day Trips
- Best Beach Towns In New England
- Things To Do In Boston In The Fall
- Gorgeous New England Islands Worth Visiting
- My Unforgettable Boston To Bar Harbor, Maine Road Trip Itinerary
That’s A Wrap On The Best 7 Day New England Road Trip Itinerary
Hopefully you’re now feeling ready to tackle planning your own adventure with this 7 Day New England Road Trip Itinerary! Even with 7 days, you can see so much of this gorgeous region and really cover a lot of ground. And, of course, if you have time to follow along on my 10 Day New England Road Trip Itinerary, that’s even better. But regardless of what you have time for, New England is always a good idea, and is always worth making time for. Happy planning!
