One of my favorite things about living in Boston is being so close to so many amazing places, whether it’s restaurants, stores, or the next destination. Living in the same city as an International airport makes it incredibly easy to get almost anywhere. However, there are SO many amazing places within driving distance that are worth visiting. In the summer, I like to travel as much as possible, so sometimes that means taking day trips rather than staying the night in a destination (have to save money somehow 😉 ). While all of these destinations are certainly worthy of a weekend overnight trip, you can also see and do a lot in just a day trip. Continue reading for my recommendations for 5 New England day trips you need to take. You can also scroll all the way to the bottom of the post for other New England destinations that are worth visiting but might be better as an entire weekend trip.
NEWBURYPORT, MASSACHUSETTS
Newburyport is just thirty five miles North of Boston and is about an hour’s drive, depending on traffic. I first fell in love with Newburyport a few years ago when I was in town before and after a wedding at Willowdale Estate (which, by the way, if anyone’s looking for a New England wedding venue, this place was insanely magical). Newburyport is one of those towns that in my book, has it all; Amazing restaurants, oceanfront views, a quaint and cute downtown Main Street, and a beach close by. Because Newburyport is just an hour North of Boston, it’s certainly do-able as a day trip without spending the night. You can start (or end) your day at the beach at Plum Island and then enjoy a couple meals or light snacks at some of the amazing restaurants downtown.
NOTABLE SPOTS / THINGS TO DO:
- Plum Island Beach
- Have dinner at Brine (great selection of oysters; the halibut is delicious)!
- Get drinks and appetizers at The Poynt (love the wood fired meatballs and their Swiss Mule cocktail)
- Get coffee at Plum Island Coffee Roasters while overlooking the water
- Shop at Sea Bags (nautical style bags made out of sailboat sails)
- Parker River National Wildlife Refuge
- Shop at Bobbles + Lace
- Get drinks at The Paddle Inn (they have such a cute surf theme)
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The brown butter lobster roll at Eventide Oyster Co. in Portland
PORTLAND, MAINE
Being a born and raised Mainer, I had to include this one because it’s one of my favorite cities and honestly, where I hope to buy a house someday when I grow up (lol). Portland has such an amazing food scene (better than Boston’s in my honest opinion), has a great downtown, and has a booming art scene. While I do think that Portland is worth an entire weekend, it can be done on a day trip if you don’t have the time or money for an entire weekend there. However, if you can afford it and have the time, you should definitely stay in Portland for the entire weekend. One of my favorite places to walk around in Portland is through the Old Port and Fore Street. There’s plenty of amazing places to eat and cute places to shop.
NOTABLE SPOTS / THINGS TO DO:
- Have lunch at Eventide Oyster Co. (amazing oysters and home to their world famous brown butter lobster roll; You can read more about Eventide in my post about them here)
- Get drinks at Central Provisions (has a bit of a hipster, speakeasy vibe and it’s awesome).
- Have dinner at Fore Street (my favorite restaurant on this entire planet. Reservations book up very quickly, but insider tip: you can walk in at 5 PM to get yourself on the night’s waiting list. I usually choose the later seating option so that I can continue to walk around Portland).
- Get donuts at The Holy Donut
- Shop at Alaina Marie (you can read more about their Maine-made, woman run business in my post here).
- Take the ferry to Peak’s Island
- Try duck fat french fries at Duckfat
- Allagash Brewing Company
- Portland Museum of Art
- Get in a good foot soak at Soakology
- Although technically Cape Elizabeth, Portland Head Light is always worth a visit and has a huge lawn for kids and/or dogs to play
- Shop at Sea Bags for beautiful nautical-style bags made out of sails
- If you decide to stay the night, stay at The Press Hotel or the Portland Harbor Hotel
- Sip wine with a wine tasting at Cellardoor at the Point
- Get coffee at Tandem Coffee Roasters or Bard Coffee
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ROCKPORT, MASSACHUSETTS
My college roommate is from Rockport, so I’ve been a few times, although I will admit I haven’t explored it as much as I hope to. Rockport has some of the freshest seafood (think right off the boat, fresh) that you can get in Massachusetts. It’s the kind of small town that’s 100% New England and reminds me a lot of a couple of the towns near where I’m from, Camden and Rockport, Maine. Rockport is also next to Gloucester (and some of my things to do below are), so you can certainly have time to visit both while on your trip.
NOTABLE SPOTS / THINGS TO DO:
- Have a beach day at Long Beach
- Shop at Wicked Peacock (jewelry + accessories)
- Get a lobster roll at Roy Moore Lobster Co.
- Get Ice Cream at The Ice Cream Store via Bri Rinehart
- Shop at Milk + Honey via South End Style
- Halibut Point State Park
- Hammond Castle Museum
- Eastern Point Lighhouse
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NANTUCKET, MASSACHUSETTS
Nantucket is an island just off the coast of Massachusetts and is a popular summer destination among celebrities and those looking for a luxury New England getaway. While I haven’t been to the Hamptons before, many people think of it as the Hamptons of New England. Nantucket certainly doesn’t come cheap, but its beauty is unmatched. While a day trip to Nantucket from Boston is a long day, it can certainly be done, and I did it this summer. You can read about my day trip to Nantucket here. Your best bet to get to Nantucket from Boston is to drive to Hyannis (parking is only $20 a day) and to take their earliest Hy-Line ferry. You can find the Hy-Line ferry schedule here. When I took the ferry it was extremely easy and everyone working was incredibly nice. The other option is to fly to Nantucket from Boston via Cape Air, but for a day trip, I would say you’re better off taking the ferry.
NOTABLE SPOTS / THINGS TO DO:
- Get sandwiches at Provisions
- Get coffee at Handlebar Café
- Cisco Brewers, + also make sure to get a lobster roll at 167 Raw if their food truck is there. Best lobster roll I’ve ever had at their Charleston location. You can read more about it here).
- Go to Brant Point Light
- Eat a lobster roll at Cru
- Shop at The Skinny Dip
- Get donuts at Downyflake via The College Prepster
- Get frosé at Brant Point Grill (they also have a great brunch menu)
- Get ice cream at The Juice Bar
- Eat at Galley Beach via Gal Meets Glam
- Rent bikes
- Have a beach day at Jetties Beach or Surfside Beach
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PROVINCETOWN, MASSACHUSETTS
Provincetown, often known as P-town, is one of those towns on Cape Cod that seems like it will take forever to get to (it’s at the very end of the Cape), however, when taking the ferry from Boston, it’s actually not bad at all; You can get to the outer hook of Massachusetts that is Provincetown in about 90 minutes. If you’re looking for a Provincetown vibe but are located a little more North than Massachusetts, Ogunquit, Maine is a similar vibe to provincetown.
NOTABLE SPOTS / THINGS TO DO:
- Eat at the Central House (my friend Michele Ragussis who I used to work for is a Food Network celebrity chef + her food is out of this world. You can find the dinner menu here + the lunch menu here).
- Eat a lobster roll at The Canteen via Domestikated Life
- Rent bikes
- Race Point Lighthouse
- Race Point Beach / Herring Cove Beach
- Have a clambake at The Lobster Pot via Domestikated Life
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OTHER NEW ENGLAND TRIPS WORTH TAKING (SOME ARE FURTHER THAN OTHERS SO YOU MAY WANT LONGER THAN A DAY TRIP):
- Rockland, Maine / Owls Head, Maine (my home 🙂 ) You can read about my weekend at 250 Main Hotel here (A MUST STAY).
- Camden, Maine (you can find my travel guide here)
- Rockport, Maine (Note: Owls Head, Rockland, Camden, + Rockport can be done in one trip together)
- Martha’s Vineyard
- Block Island, Rhode Island
- Newport, Rhode Island
- Stowe, Vermont
- Ogunquit, Maine
- Portsmouth, New Hampshire
- Kennebunkport, Maine
- York, Maine
- Burlington, Vermont
- Provincetown, Massachusetts
- Cape Cod, Massachusetts
- Salem, Massachusetts
- The Berkshires, Massachusetts
- Scituate, Massachusetts
What’s your favorite New England town or city to road trip to? Let me know in the comments!
If you don’t want to rent a car but would like to do a day trip outside of Boston, is that possible with public transportation? Thanks!
Hi Deandra, that totally depends on where you want to go! Uber is readily available, and you could definitely take the commuter rail if your destination is along that route. Typically the commuter rail has a set schedule where every hour on the hour, you could get on a train, but I would suggest taking a look at the schedule and the destinations. Another really cool thing to note is that in the summer, you can get on the ferry in Boston and take it to Provincetown which would be a great day trip! Taking the ferry there is much quicker than driving. Let me know if you have any other questions 🙂 and thanks for reading!