New England,
close to home.
You don't need a flight for most of this. Northern New England especially rewards a family willing to just get in the car: walkable harbor towns, real coastline, and a Saturday that doesn't need a passport. Guides for the weekends, articles for what's in season right now. We're based in New Hampshire, right on the Maine border, and give drive times from Boston because that's where most readers set out.
Real 2026 dates and family tips for 10 MA fall festivals, from the Avenue of States at The Big E to the Shuck-Off at Wellfleet OysterFest.
Read the article →A New England vacation or a flight?
Two very different kinds of trip.
A New England weekend and a two-week trip to Portugal solve different problems and need different amounts of planning. Northern New England is the one you can do on a whim: pack the car Friday after work and be walking a harbor town by dinner. If you're weighing something that needs a flight instead, that's what we call And Beyond, and it's also where our paid planning service actually earns its keep.
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Walkable downtown, a real working harbor, and the Coastal Maine Botanical Gardens as a full second day. We did it with a toddler and a baby and never touched the car once we arrived.
North Conway, Vermont, Portsmouth, Ogunquit, Cape Cod, the Berkshires and the White Mountains, ranked by drive time and by what there is to do once you park.
Portsmouth NH, the Hampton and Rye beaches, Ogunquit, Kennebunkport and fall farm days, ranked by drive time.
What our girls ask for every time: Prescott Park, Market Square, two museums just outside town, and the Rye and Hampton beaches.
The seacoast, Mount Major and Gunstock, Ice Castles and the Cog Railway, Story Land and North Conway, and fall fairs, region by region.
Story Land when the girls were under 6, the village and outlets, Tuckerman and Moat Mountain for dinner, and the hotel we loved.
Kyle grew up in Wallingford. Woodstock and Quechee, Killington, Stowe and Burlington, and when to go.
Peak color by sub-region, real dated fall events, and apple picking, all in one place. Grew out of our fall Instagram series.
Hampton Beach's Seafood Festival, Topsfield Fair, a pumpkin-boat regatta in Damariscotta, and seven more, with dates, admission and family tips for each.
The NH Highland Games, the Winchester Pickle Festival, Deerfield Fair, RiverFire, and six more, with dates, admission and family tips for each, state by state.
The Big E, King Richard's Faire, Topsfield Fair, Salem's Kids' Fun Fest and six more, with dates, admission and family tips for each, state by state.
Kailah was born and raised in New Hampshire. The running list we're working through with our own girls, started as two Instagram posts.
Bay-side beaches, a carousel, and a Martha's Vineyard day trip built around ice cream and candy.
Lenox, Stockbridge and Great Barrington, an easy hike with a real payoff, and Tanglewood's lawn.
Ice Castles, the Mount Washington Cog Railway, and Woodstock Inn Brewery, from a family that goes up there year-round.
Portland for an easy day trip, Bar Harbor and Acadia for the bigger payoff. The two other Maine towns we've actually taken the girls to.
Cape Cod, the Berkshires, the White Mountains and Boothbay Harbor, compared side by side.
The both-parents-must-appear rule, current fees, and what our own post-office appointment actually looked like.
Maple sugaring season, mud season's back roads to avoid, and April vacation week.
Ice Castles, a Dickens-themed maritime village, and four Gilded Age mansions strung with lights.
The Tunbridge World's Fair, the Stowe Foliage Arts Festival, and eight more, state by state.
A Currier-and-Ives horse parade in Woodstock, and a free kids' train looping a 30-foot Christmas tree in Burlington.
The Fryeburg Fair, the Camp Sunshine Pumpkin Festival, and eight more, beyond Boothbay.
Kennebunkport's Christmas Prelude, Gardens Aglow at Boothbay, and eight more.
Ice Castles, Santa's Village, and a European-style Christmas market in Waterville Valley.
The Faneuil Hall tree lighting, Christmas by Candlelight at Old Sturbridge Village, and eight more.
If the girls had been a little older or the day a little warmer, we'd have booked the Boothbay whale watch ourselves. GetYourGuide is where we check for tours and cruises like it before a trip.
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Maine beyond Boothbay Harbor and a dedicated fall foliage guide are next on our list for this cluster, because a single card doesn't do either justice.
Questions, answered
What is there to do near Boston with kids in New England?
Our top pick is Boothbay Harbor, Maine: about 3 hours, a walkable downtown, and the Coastal Maine Botanical Gardens as a full second day. Closer in, Portsmouth, NH is about an hour away and works as a day trip or an easy overnight.
Is northern New England good for a family trip?
Yes, and it's underrated compared to the well-worn Cape Cod and Berkshires routes. The Maine coast north of Boston has walkable harbor towns, real coastline, and far less summer traffic than the Cape. Boothbay Harbor is the guide we send people to first.
Do Northern New England trips require a flight or a passport?
No, that's the entire point of this section. Everything here is a drive from Boston, and the main destinations, from Portsmouth, NH at about an hour to Boothbay Harbor at about three, are all within about three hours. For guides to the trips that do need a flight, see And Beyond instead.
What's the best New England weekend trip for young kids?
Boothbay Harbor lets you park once and walk everywhere, which matters more with a toddler than anything else on this list. We did Boothbay Harbor with a toddler and a baby and never needed the car once we arrived. For the mountains, North Conway: we took both girls to Story Land when they were under 6.
What's the difference between a guide and an article here?
Guides are full destination write-ups like Boothbay Harbor: where to stay, what to do, day by day. Articles are shorter and often seasonal, like our fall events roundup or the family experience lists we post to Instagram first. Use the filters above to tell them apart.
What are the best day trips in New England with kids?
The easiest New England day trips with kids are on the coast just north of Boston: Portsmouth, NH and the Hampton and Rye beaches at about an hour, Ogunquit's Marginal Way at about 1 hour 15 minutes, and Kennebunkport's Dock Square at about 1 hour 30 minutes. Our day trips from Boston guide ranks them all by drive time.
What are the best New England vacations for families?
The ones we send people to first: Boothbay Harbor for a walkable Maine harbor town, the White Mountains for the outdoors in any season, and Cape Cod or the Berkshires for beaches or small towns. All are within about 3 hours of Boston, and our New England getaways index matches them to what your family wants to do.
The trip after this one
might need a flight.
Once a family has done a few New England weekends, the next question is usually Europe. That's what And Beyond is for. If you want help with that one, we offer a $99 planning consultation, or we book the flights, the stay and the activities for you from $499.
The flight guide from Boston.
Which routes run year-round, which are summer only, how far ahead to buy for a school vacation week, and the order we book a trip in, for when Northern New England turns into And Beyond.
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