There’s a version of New England travel that’s all foliage-weekend traffic and fully-booked inns, and there’s a version where you already know where you’re going before everyone else starts googling “best fall trip New England.” This week we’re handing you the second version. We enjoy both versions, but some of the best adventures take just a bit more planning.
We put together a season-by-season list of twenty adventure weekends across the region: five for spring, five for summer, five for fall, five for winter. Each one comes with a home base, a short list of things worth doing while you’re there, and some of my local tips from actually doing it - it’s your ideas list for 20 adventures.
We’re done some of these and the other weekends are on the list for the next year, but are worth mentioning.
Since we’re deep in foliage planning right now, here’s a taste of what’s on the list:
White Mountains foliage road trip, NH Early-to-mid October on the Kancamagus is New England at its most iconic, a few summit hikes for the view from above, mountain-town stops in North Conway and Jackson. The tradeoff: it’s also some of the heaviest traffic of the year, so a weekday drive or an early start earns its keep.
Berkshires foliage and farm weekend, MA Less about the drive, more about everything around it, a Greylock summit for the view, an orchard stop, a stretch of afternoon at Mass MoCA or the Clark. Lodging in Lenox and Stockbridge goes fast, so this is a book-a-month-out kind of weekend.
Litchfield Hills weekend, CT Connecticut’s quiet answer to Vermont and the Berkshires — stone walls, small green-centered towns, short hikes at Macedonia Brook or Kent Falls. If you want color without the crowds, this is the backup plan worth knowing about.
Acadia in autumn, ME Cooler hiking temperatures, thinner post–Labor Day crowds, and sunrise from Cadillac Mountain over changing leaves. The one thing to lock in first: the Cadillac summit road reservation, before you plan anything else around it.
That’s four of the twenty. The full guide also covers spring waterfall hunts, a Maine windjammer cruise, a Green Mountains backpacking loop, three different ski weekends, and a dozen more: all mapped by season, so you’re never wondering where to go next.
The full 20 Weekend Adventures guide is our latest paid-subscriber perk. It’s yours the moment you upgrade: a keeper of a list to pull out any time you’re staring at a blank weekend and want to already know where you’re headed.
The River Nobody Talks About (And Why That’s About to Change)
The Connecticut River runs 410 miles from the Canadian border to Long Island Sound, through four states, past some of the oldest towns in America, and alongside farmland that has been in continuous cultivation since the 1600s.