Weekend getaways from Boston,
ranked by drive time.
Not every trip needs an airport. These are the weekends we actually take with our two girls, from Portsmouth to the Vermont towns Kyle grew up around. We live on the New Hampshire seacoast, but the drive times here are from Boston, where most readers start. Two regions we know as adults but haven't done as a family are marked as research.
What are the best weekend getaways from Boston with kids?
Boothbay Harbor, Maine is our strongest all-around pick: about 3 hours, a walkable downtown and a real working harbor, with no car needed once you park. For the mountains, North Conway, NH is where we usually stay over with the girls. Portsmouth, NH is the short one, at about an hour. Past 3 hours each way, a two-night weekend shrinks to one real day.
| Top pick | Boothbay Harbor, Maine, about 3 hours |
|---|---|
| Shortest drive | Portsmouth, NH, about 1 hour |
| Mountains, with an overnight | North Conway, NH, about 2.5 to 3 hours |
| Vermont | Woodstock and Quechee about 2.5 hours, Rutland and Killington about 3 |
| Beaches | Ogunquit, Maine, about 1 hour 15 minutes. Cape Cod, about 1.5 to 2 hours (research-based guide) |
| Passport or flight | Neither. Everything here is a drive |
How we ranked these.
Three things decide whether a weekend trip is actually worth planning around with young kids: how long you're in the car, whether there's a real reason to get out of it once you arrive, and whether the town itself is walkable enough that a stroller or a tired 6-year-old isn't fighting you the whole time. Distance is the easiest of the three to get wrong. A place that's "close" on a map can still be a bad Saturday if the drive is all highway and the payoff is a single overlook.
The best weekend trips from Boston,
ranked by drive time.
We go often with the girls. Prescott Park, Market Square and the downtown shops, then the Children's Museum of New Hampshire in Dover or the Seacoast Science Center in Rye when they want something hands-on. Close enough to do as a day trip, too.
Our guideFor the girls, Ogunquit is two things: the Marginal Way and Ogunquit Beach. That fills a day, and an overnight saves the sandy drive home. It sits on our day-trips list for a reason.
Kyle knows the Cape well as an adult, but we haven't done it with the girls, so this guide is built from research. The bay-side beaches are calmer and warmer than the Atlantic side, and the Flying Horses Carousel on Martha's Vineyard makes an easy ferry day. Plan around the summer bridge traffic.
Ice Castles and the Cog Railway in winter, real hiking with kids the rest of the year, Woodstock Inn Brewery whenever a table's needed. We go up there year-round.
Western Massachusetts, and a genuinely different landscape from the coast: small walkable towns paired with an easy hike and a real payoff view. Built from research, not a family trip, and the guide says so.
Kyle grew up in Wallingford, and we're back in the Rutland and Killington area to see family all the time. With the girls we've also done Woodstock and Quechee (about 2.5 hours), Stowe, and Burlington on Lake Champlain (both about 3.5). Summer and fall are the best of it.
Our guideWe usually drive up and stay over with the girls. Most recently that was the White Mountain Hotel and Resort, which we loved, and we've also stayed at one of the motels right in town. Story Land when both girls were under 6, the village and the outlets for shopping, and Tuckerman Brewing and Moat Mountain Brewing, both kid-friendly. Without the kids, the Bernerhof Inn is super cozy.
Our guideWalkable downtown, a real working harbor, and the Coastal Maine Botanical Gardens as a full second day. No car needed once you've parked. This is the trip we send people to first.
Our guidePortland is an easy coastal stop. Bar Harbor and Acadia National Park are the biggest payoff on the Maine coast, and far enough that we treat them as a long weekend rather than a regular one.
Our guideDrive times are approximate, from Boston in normal traffic. For dated reasons to go, see the Vermont fall events list, and for trips that don't need an overnight, our day trips from Boston.
The questions we actually get asked.
Boothbay Harbor, Maine is our strongest all-around pick: about 3 hours, a walkable downtown, and a real harbor to look at without needing a car once you arrive. For the mountains, North Conway, NH is about 2.5 to 3 hours away and is where we usually stay over with the girls. For a shorter drive, Portsmouth, NH is about an hour.
Most of the trips worth the drive fall between 1 and 3 hours. About an hour covers Portsmouth, NH, with Ogunquit, Maine a little past that. The 1.5-to-3-hour band covers Cape Cod, the White Mountains, the Berkshires, Woodstock and Quechee in Vermont, North Conway and Boothbay Harbor. Past 3 hours it becomes a long weekend or a flight, which is a different list.
Past about 3 hours each way, a two-night weekend turns into one real day once you subtract both drives. Stowe, Burlington and Acadia all sit past that line, so we save them for a long weekend. Everything else on this list stays under it.
Portsmouth, NH. About an hour each way means you can leave after breakfast and still have a full afternoon at Prescott Park and Market Square. See our full day-trips list if an overnight isn't in the cards.
No, that's the point of this list. Everything here is a drive from Boston. For the flying version of this question, see every nonstop from Logan instead.
North Conway, where we took both girls to Story Land when they were under 6. Portsmouth is the closer option, with the Children's Museum of New Hampshire about 15 minutes away in Dover.
Portsmouth, NH at about an hour and Ogunquit, Maine at about an hour and 15 minutes are the closest to Boston of the trips we take with the girls. Boothbay Harbor at about 3 hours is the farthest we'd still call a weekend getaway rather than a trip that needs its own vacation day.
From a Boston starting point: Boothbay Harbor for the Maine coast, North Conway and the White Mountains for year-round outdoors, and Vermont in summer and fall. Cape Cod for beaches and the Berkshires for small towns are research-based guides, and they say so. Our New England getaways index sorts them by what your family actually wants to do.
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.
Or have us plan it with you: a $99 consultation, or full booking from $499.