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THE THING BEFORE PREPPY

Tuesday, March 31, 2026

Best Vacation Spots in New England for a family in Summer?

 Here is a question for the community:

What are your favorite spots in New England for a family vacation in summer?  If you have two or three, can you rank them?

19 comments:

  1. If you want some quiet and some space, Bar Harbor right after July 4 is nice. My wife and I honeymooned there, and we timed it just right.

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  2. I love Block Island. Find an old cottage out on the bluffs to rent and you will have a lovely time.

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  3. The Taconics. The Presidential Range. The High Peaks.

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  4. Get away from all the congestion. All of it. Find a quiet lake high up in the hills and off the beaten path in Maine or New Hampshire. One that doesn’t allow motorboats. Stay a couple of weeks. There may be a town nearby. But only go there, once or twice, to buy the Sunday papers and to buy your vegetables and cheese at the farmers market. Buy your steaks, burgers and hotdogs at the local IGA. Forget about doughnuts and croissants. BYOB. Eat soft scrambled eggs when you get out of bed especially if it’s in the middle of the morning. Don’t hold noisy parties because sound travels over water and you don’t want to disturb the others on the lake enjoying the peace and quiet. In the unlikely event one of the few neighbors decides to play loud music call the ranger and they will come and put a stop to that toute de suite. Let your kids fish for sunnies and look for salamanders. Don’t mention miniature golf. Don’t move when you see a deer. Take naps in the shade of the porch in the middle of the afternoon. Read old mysteries and that book of Donald Hall poetry left behind by a previous visitor. Pray for rain in the middle of the night that will wake you with the pitter patter of the raindrops falling on the leaves of the trees. Turn over and go back to sleep. Laugh a lot… There’s a place actually in Connecticut that fits this description. But you’re crazy if you think I’m going to tell you where it is.

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  5. It’s not “salt water” New England, but the Woodstock, VT area is great for a family vacation. There are things to see and do in town, and then you are within driving distance to Billings Farm, the Vermont Country Store, Simon Pearce, covered bridges, and more. Nearby ski resorts have fun mountain coasters that younger kids absolutely love. If it is feasible, staying at the Woodstock Inn is worth it no matter what time of year. One of my favorite summer trips in recent memory.

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  6. Portland and the surrounding smaller towns and islands.

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  7. We vacation with extended family every summer: my parents, my brother and sister, spouses, kids, nieces/nephews & some significant others. Usually 15-20 of us, depends on work schedules for the 'kids,' all young adults in post-college/pre-marriage period of their lives.

    Beach, have liked places near Brewster & Chatham on Cape Cod, but there are many great places to stay. Southern and Central Maine coast, we've stayed in York and near Rockport; and a few different places on Martha's Vineyard. It's not easy to find properties than can handle all the people; we angle for places that are a little out of the mainstream, less busy neighborhoods and beaches.

    We have also liked staying on lakes with access to good paddling and hiking: Meredith NH and other places around Lake Winnipesaukee, Lake Placid area in NY, which isn't New England but feels pretty similar; Rangeley Lake, which is northwestern Maine near the Vermont and Canadian borders.

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  8. Well, there is no best answer because it depends on what you are looking for. I love the North Shore of Massachusetts from Marblehead up to Newburyport. It has everything from hidden coves and picnic spots, to breathtaking beaches, to historic buildings and lighthouses, to lobster shacks, to fine dining, to world class sailing, to whale watches, to outstanding museums. Something for everyone and every mood. On the other hand, it is not exactly secluded.

    If you are looking to get away from at all, you cannot do better than an island in Penobscot Bay.

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  9. Great advice. New England is varied and wonderful in summer generally. But Martha’s Vineyard is not Maine - it’s not even Nantucket. It depends on what you want to do, who you are, and who you want to be around. But above all, if it’s not here, you probably shouldn’t want to do it.

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  10. You’re right. Nantucket is a hot and sandy spit. Martha’s Vineyard has an agricultural scene (small but nonetheless) that gives it a certain joie de l’été.

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  11. Growing up in the 70s, my parents tried to get us to the Cape each summer. We (they) rented houses around Chatham. One year my mother put her her foot down — renting a house was not a total vacation for her as she still had to cook and tidy up. We then got a few rooms at the "Wayside Inn" in Chatham (most likely something else now). Us kids were in our teens — being in town suited us — more to see and do.

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  12. Darn it, too late to say anything original. With the caveats that it depends on personal preference, and that there are so many great choices, my favorite remains Chatham.

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