But really…is there anything better than a New England Road Trip?? I think not. And today I’m going to tell you ALL about the awesome Summer New England Road Trip I took. You may have already read my separate travel guides for Boston, Portland & Portsmouth, but in this post you’re going to find my exact New England Road Trip Itinerary plus lots of substitutions to make this the BEST road trip ever.
To be honest prior to this year I wasn’t a huge fan of road trips. I was more of a “get me on a plane and to my destination” type of traveler, but after my Florida Keys Trip where Megan and I spent 5 days driving from Miami all the way down to Key West and back I developed a whole new appreciation for them.
There are so many places I have on my American bucket list, but in years past I sometimes passed them over for trips to more exotic locales, now I’m finally getting a chance to knock a few of those off my list and I encourage you to do the same and take the time to explore the United States!
New England is the northeast region of the United States comprising of the states of Maine, Vermont, New Hampshire, Massachusetts, Connecticut and Rhode Island. It’s known for its Colonial past and rich history, Atlantic coastline, small seaside towns, fall foliage, national parks and outdoor adventures! It’s the birthplace of America and no where else in the country can you find white sand beaches, lighthouses, expansive lakes, mountain views and more in such a condensed area. And no matter what type of traveler you are New England has something for you!
I’ve lived in New York my entire life and there are SO many places that are just a car ride away that I haven’t visited yet, so if you’re the same THIS IS YOUR SIGN to book that trip!!
New England Road Trip Itinerary
Day 1 – Boston, MA
- Drive to Boston. From Westchester it takes just over 3 hours so we left around 9:45 and got there right around 1pm.
- Check into your hotel. We were able to check into our hotel – Boston Park Plaza – right away, but if not you can easily have wherever you’re stayed hold your bags for you until your room is ready.
- Have lunch at The Banks Fish House – I highly recommend ordering the Unicorn Oysters, Fried Artichokes, Steamed Mussels, a Lobster Roll & The Chowda Flatbread!
- After lunch explore Boston’s Back Bay, Boston Common Park, Beacon Hill (my personal favorite Boston neighborhood) and made sure to snap a photo on Acorn Street (the most photographed street in America)
- Head back to the hotel to freshen up (and check in if you couldn’t earlier).
- Take an Uber to dinner at Bar Mezzana in Boston’s South End’s Ink Block Neighborhood – order the Black Truffle Burrata, Paccheri with Lobster and Orecchiette.
Day 2 – Boston, MA
- Start your morning at Tatte Bakery for the BEST pastries you will have in your life. I’m not even exaggerating, we were in Boston for 3 days and came to Tatte 3 times. Order the Pistachio Croissant!
- After breakfast explore Downtown and Boston Harbor. Make sure to walk along the Freedom Trail and past Brattle Book Shop, Old State House, Quincy Market and Faneuil Hall – especially if it’s your first time in Boston.
- Head over to Boston’s Seaport District for brunch on the water at Woods Hill Pier 4. Order the Salad of Mixed Greens with Grilled Chicken, Heirloom Tomato Salad, WHP4 Burger and the Lobster Popover.
- After lunch take an Uber over to Boston’s North End for cannolis at Mike’s Pastry & Modern Pastry (find out my favorite in my Boston Travel Guide)
- Walk back over to the hotel to rest for a little and then head to dinner at Saltie Girl off Newbury St. Order the Clam Chowder, Snow Crab Toast, Torched Salmon Belly, Warm Spicy Crab Roll, Hand-Chopped Dry Aged Steak Tartare, Rock Crab Carbonara and Ginger Scallion Lobster.
Day 3 – Boston & Portland
- Start your morning at Tatte Bakery (yes it’s that good, trust me)
- Walk over to Boston Public Library in Copley Square. Just a heads up the library is closed on Sunday, so hopefully your day 3 won’t be a Sunday and you’ll be able to go in and explore unlike us.
- Take an Uber over to Fort Point for brunch at Lolita Cocina & Tequila Bar. Order the Guacamole Fresco, Mushroom Empanadas, Tuna Maracuya, Lolita Lobster Roll (topped with Mexican corn!), Mushroom Quesadilla and Broken Eggs.
- Head back to the hotel to grab your bag and get on the road.
The drive to Portland, Maine should take you just under 2 hours.
- Once in Portland, checked into your hotel – we stayed at The Blind Tiger (get my full review of it here). And head right out to walk to dinner.
- Have dinner at Scales, Boone’s Fish House & Oyster Room, Portland Lobster Company or Leeward.
PORTLAND TIP: MAKE RESERVATIONS FOR DINNER EVERY NIGHT! IT’S REALLY DIFFICULT TO GET A TABLE AS A WALK IN.
Day 4 – Portland, ME
- Set your alarm for 4:30am to make it to the Portland Head Light for sunrise. While it was really rough getting up that early it was definitely worth it. Make sure to dress warm even in the summer because it gets chilly.
- Stop at The Holy Donut for a half dozen of their infamous Maine potato donuts. Just trust me this is a MUST stop.
- Head back to the hotel for a nap (we needed it after the early morning), then get ready for the day.
- Have lunch at High Roller Lobster Company. We ended up ordering their famous build your own lobster roll to go and sat in a nearby park to eat.
- Checked out a few of Portland’s local craft breweries. We visited Austin Street Brewery & Rising Tide Brewing Company, but check out my Portland Guide for more suggestions.
- If you can’t get a reservation ahead of time at Eventide Oyster Co., then at 5pm, walk over to put your names down on their reservation list. We didn’t end up getting a seat so we ordered takeout from there to bring back to the hotel to eat. Order the Eventide Brown Butter Lobster Roll, Tuna Tostada & The Fish Sandwich.
Day 5 – Portland, Kennebunkport, Ogunquit & Portsmouth
- Started your day with breakfast. We ate at our hotel, one of the the perks of staying at The Blind Tiger (or any other Lark Hotels) is that they offer the most delicious complimentary breakfast small plates.
- After breakfast check out and head south!
If you have more time continue north to Bar Harbor, Maine, it’s about a 3 hour drive and one of the most picturesque coastal towns in the Northeast. It’s located on Mount Desert Island along Maine’s Frenchman Bay and serves as a gateway to the mountains and cliffs of neighboring Acadia National Park.
Next stop, Kennebunkport!!
- Have lunch at Alisson’s Restaurant right in the middle of town. Order whatever Allagash Brewing Company they have on tap and the Maine Lobster Cobb Salad and the Happy “Gil”more Sandwich!
- Then spend a little bit of time exploring roaming the streets, swooning over the perfect houses and shopping in the cute souvenir stores in this small town!
Then hit the road again and stop 11 miles down the coast in Ogunquit, ME.
- Explore Perkins Cove – originally a small fishing community and artists’ colony, the Cove is a charming area that consists of local independent shops, restaurants and scenic outlooks. Hugged by the Atlantic Ocean on one side and a small harbor on the other side, guests can picnic on the rocks while enjoying the crashing surf, stroll across the footbridge and check out the boats, enjoy picturesque dining with southern Maine’s most beautiful views, or book a fishing or sailing trip to enjoy land views from the ocean.
- If you have more time here grab a lobster roll at the Lobster Shack!
- Then get back on the road to your final destination Portsmouth, NH!
- Check into your hotel – we stayed at Hotel Portsmouth – then head right out to dinner at Moxy, a modern American tapas restaurant focusing on smaller plates meant for sharing. The menu is seasonal and always rotating, but if they’re on the menu order Tuckaway Corn Muffins, Fried Pickle Chips, Pork Belly Bites, Fried Clams, Potato Gnocchi, Misty Knoll Farms Pan-Seared Chicken Tights and Beef Short Rib Marmalade.
Day 6 – Portsmouth, NH
- Spend the day exploring downtown Portsmouth – a few great places to visit are Strawbery Banke Museum, Prescott Park and more!
- Have lunch at Portsmouth Brewery, order the Torn & Frayed IPA and Surrender to the Flow IPA to drink. And the Carnitas Loaded Fries and Brew Love Burger to eat.
- Make sure to shop in all the cute shops in Market Square – Wiglesworth’s Mercantile was one of my favorites!
- Go to happy hour at The Franklin Restaurant! Try to get a seat at the horseshoe shaped oyster bar. Order champagne and oysters from the happy hour menu!
- Take a sunset sail with Portsmouth Harbor Cruises.
- For more information on what to do and eat in Portsmouth check out my Portsmouth, New Hampshire Travel Guide.
Day 7 – Portsmouth & Drive Home
- Check out of your hotel and drive home!
If you’re looking to extend your trip I suggest driving from Portsmouth to Newport, RI and spending the night there! It’s the perfect place to explore for a day or two no matter what season it is!
If you’re looking for another few days of road trip fun I would go to Cape Cod if it’s the Summer or over to Vermont if it’s the Fall or Winter! You can follow my Complete Vermont Fall Travel Guide for the perfect 5 day trip visiting Stowe, Woodstock and Burlington!
New England Road Trip Tips
The best Time of Year to Visit
I personally think the best time of year to do a New England Road Trip is during the Summer or Fall. You can’t go wrong during either of those seasons in all of the New England states. During the Summer you’ll be able to take full advantage of the coast and beautiful beaches and during the Fall, New England is the BEST place to be for leaf peeping. Make sure to check the yearly Fall Foliage Calendar to find out exactly when the leaves will be changing that year to properly plan your trip.
If you’re into skiing and snowboarding then I suggest booking a trip to New England during the Winter! New England is home to some great mountains like the Green Mountains in Montgomery, VT, Mt Mansfield State Park Forest just outside of Stowe, VT and White Mountains in Lincoln, NH. And if you happen to be near these areas when there isn’t snow on the ground many of them become hiking trails during the off season.
What to bring
- Extra layers of clothing – No matter what the season, when you’re traveling in New England the weather and climate can drastically change depending on your location because of the different terrain and elevation! In the mountains and on the coast it can be much cooler than in land.
- Comfortable sneakers – Whether you’re exploring or casually wandering the last thing you want to happen if for your feet to start hurting in the beginning of your trip!
- Travel pillow, blankets, eye mask, etc. – You’re going to be spending a lot of time in the car so make sure you’re comfortable and can sleep if you need to!
- Roadside emergency kit & first aid kit
- License, registration and insurance!
- Bug spray
- Sunscreen & sunglasses
- Phone chargers & USB cords
- Toilet paper, hand sanitizer, painkillers, etc. – Rest stops aren’t always the most stocked so these could save you!
- Reusable shopping bag
- Snacks & garbage bags
what to consider before stopping at each place
- How long are you staying?
- Are you staying overnight?
- Is there safe parking?
- What activities are you planning to do at this stop?
- What’s the weather?
New England Cities I recommend visiting if you have limited time:
If you don’t have a lot of time I suggest visiting just one city! All of the below places can easily be weekend or long weekend trips!
other new england cities to consider adding to your trip if you have more time:
These areas of New England are great if you’re looking for a 5+ day vacation!
- Cape Cod
- A 65 mile hook shaped peninsula in Massachusetts, Cape Cod is one of the world’s most well-known summer vacation spots!
- It’s known for it’s beautiful beaches, laid back lifestyle, quaint villages, seafood shacks and connection to the Kennedys.
- This Northeast vacation destination is a perfect addition to your road trip if you’re looking to relax.
- Visit Hyannis, Provincetown, Chatham, Dennis & more!
- Northern Vermont including Stowe, Woodstock & Burlington
- Stowe is a town located at the foot of Mount Mansfield (Vermont’s highest peak) and known for it’s trails and ski slopes.
- Woodstock is a charming, quintessential Northeast village home to covered bridges, picturesque New England Countryside and more! It’s been voted the prettiest town in America.
- Burlington is a college town (home to University of Vermont & Champlain College) and a commercial city located on the eastern shore of Lake Champlain, south of the Canadian boarder. It’s known for it’s free-thinking spirit.
- Northern & Eastern Maine including Bar Harbor, Camden & Augusta
- Bar Harbor is one of the most picturesque coastal towns in the Northeast. It’s located on Mount Desert Island along Maine’s Frenchman Bay and serves as a gateway to the mountains and cliffs of neighboring Acadia National Park. Also home to Cadillac Mountain, the tallest mountain on the eastern seaboard of the the United States and the first place to see the sunrise in the U.S. in the winter. During the months of April through October, Bar Harbor is a great place to go whale watching.
- Camden is small, but it’s harbor is always bustling with boats bringing fishermen in and out all day. It’s a great place to catch a harbor cruise to check out the area’s best lighthouses and lobster habitats.
- In Maine’s capital, Augusta, you’ll find Victorian mansions, hiking trails, rich history and the oldest wooden fort in the United States.
PIN my New England Road Trip Itinerary for LATER:
Don’t miss my other popular New England travel posts:
48 Hours in Newport, Rhode Island
Best Things to Do in Portland, Maine
2 Days in Boston
My Complete Vermont Fall Travel Guide
Locations in New England – Massachusetts, Maine, New Hampshire, Rhode Island, Vermont & New York
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