Hey new englanders -best place for a weekend getaway for great food, classic New England experience, cute towns, etc?

I am from the west coast but heading to Boston for a work trip. I've never spent time outside of Boston in New England so I'd love to spend a long weekend in a New England town getting the classic experience - sunsets, seafood, hikes, quaint shops, all of it! I wasn't planning on renting a car but open to it potentially. My one thought was Portland Maine but am looking for your recommendations of places to stay/see/eat! Thanks :)

Lauren Ruben


Voted the Best Reply!

sharigale July 6, 2017
You should try Block Island. You take a ferry to get therefrom CT, and once there you don't need a car. It's super New England. You can rent bicycles and ride around the island. Gorgeous!!!
LeBec F. June 28, 2017
Hi L, it helps if you tell us WHEN you will be going because of events schedules, traffic etc. Wkend or workweek? I've been in boston 40 yrs and my favs , for your criterea- would be Portland ME and Marblehead MA, followed by Portsmouth NH. Oceanside sitting and walking, beautiful historic centers; Portld has really become the Berkeley, CA. of New Eng.
ChefJune June 26, 2017
I love Portsmouth NH. It's an easy trip by car or bus, and the town is lovely, walkable, historic, great seafood,. Don't miss Strawbery Banke.
Happygoin June 26, 2017
You could do without a car and take the commuter rail to the Gloucester/Rockport area. It's beautiful and very walkable. You might augment with Uber. Or you could take the train to Portsmouth, NH. Again, very walkable, but can augment with Uber if you like.
Jan W. June 16, 2017
Martha's Vineyard is fantastic - all of the stuff you mentioned and it's actually not that expensive to stay there if you know where to look from my experience. Food can also be very reasonable. If you don't want to bring your car, a fleet of public buses go to all of the major towns and hamlets around the island, as well as taxis. I'm not sure if Gay Head Light in Aquinnah is still being restored after being moved inland due to erosion issues, but its definitely one of the greatest places to watch a sunset in NE.

Portland is great too but it's not quaint in the small-town New England sense, it is a busy town -especially in the summer. Portland has great art galleries and numerous excellent restaurants. If you want to get away from the city, Peaks Island is a very scenic ferry ride away.

spiffypaws June 16, 2017
Kennebunk and Kennebunkport Maine are only 1.5 hours from Boston. Cape Porpoise is beautiful this time of year and there are a ton of great restaurants in Kport.
HalfPint June 16, 2017
Freeport Maine or somewhere near it. The town itself is one big but quaint outlet shopping center. There's a nearby seafood eatery that's right on the dock. Get the tourist map in town. Has a few fun places on it.

Mystic CT. Walk around the museum.

Providence RI. You can walk along the waterfront, visit all the mansions, lots of seafood. Not a small town but plenty of good walks and sunsets.

Nancy June 16, 2017
If you choose Providence and like Pizza/Italian food, check out Al Forno.
Bevi June 16, 2017
Wellfleet MA. Hike in the Audubon Center in South Wellfleet. Kayak or swim in the Kettle Ponds between the Bay and the Ocean. There are beautiful beaches on both the Bay and the Ocean. Provincetown is the quintessential end of the road town on the tip of the Cape, about a 20 minute drive (or a 1-hour bike ) from Wellfleet. Great biking with a newly installed and marked bike lane going both north and south on Route 6, but plenty of side shun pikes to take as well. Many historic buildings. Eat at The Wicked Oyster in Wellfleet, or Victors, Bubbela's, or Spiritus Pizza in P Town. You can rent kayaks in many places. There are dozens of cheap eat places in both towns. The Beachcomber is a famous Wellfleet beach bar that has music and a great outdoor but enclosed bar, as does the Pearl on the Wellfleet harbor. It's a 2-hour drive from Boston, or a 1 hour fast ferry ride. Enjoy!
paseo June 16, 2017
Midcoast Maine. Stay just about anywhere in Camden and try to eat at Nina June in Rockport, Francine in Camden, Primo in Rockland, McLoon's Lobster in Spruce Head. You would not be sorry at any of them. Head up to Belfast for lunch at Meanwhile in Belfast then walk the Harbor and River Walk. Pray for good weather.
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