Everywhere worth a weekend,
within three hours of Logan.
Not every trip needs an airport. This is the shortlist we send people to first, ranked by drive time and by what there actually is to do when you arrive — not by how the listing photographs.
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.
Ranked by drive time
from Boston.
Walkable 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 guideThe lowest-commitment trip on this list. Close enough to do as a long day if a full weekend doesn't fit, with real beaches and a harbor town that doesn't require a hotel booked months in advance.
The Cliff Walk works with kids as young as 5 if you're comfortable holding hands on the narrower stretches, and the harbor itself is entertainment on its own. Busy in summer — better as a shoulder-season trip.
Big enough that "Cape Cod" isn't really one trip — the Upper Cape and the Outer Cape are different weekends. Provincetown by ferry from Boston is its own option and skips the summer traffic entirely.
Western Massachusetts, and a genuinely different landscape from the coast — hills instead of harbor towns. Better suited to a family that's fine with more driving between stops rather than one walkable base.
The Kancamagus Highway and Franconia Notch are the draw. Strong pick in October for foliage, or in winter if a ski weekend is the plan — less built for a casual summer wander than the coastal options above.
Vermont and the deeper Maine coast beyond Boothbay Harbor get their own dedicated guides — those are next on our list, since a single card here doesn't do either justice.
The questions we actually get asked.
Past about 3 hours each way, a two-night weekend turns into one real day once you subtract both drives. That's the line between "weekend getaway" and "you should really fly." Everything on this list stays under it.
Cape Ann. Under an hour each way means you can leave after breakfast and still have a full afternoon, which isn't true of anywhere else on this list.
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.
Boothbay Harbor and Cape Ann both let you park once and walk everywhere, which matters more with a toddler than anything else on this page.
The Boston family flight guide.
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 the whole trip from $499.