Boston “Summer” Getaways That Are Even Better in Autumn

Let’s be honest: a lot of Boston-area getaways are vastly overrated during the peak season. There’s the traffic, the tourists, and — let’s just be honest — too many people. Look, we’re not anti-social or anything, but nobody in their right mind has ever has said, “Oh, let’s go to that charming little seaside restaurant; it’s always packed with screaming crowds, it’s delightful.” Fall is really where it’s at, especially in these top spots!



Summertime in Nantucket is a little nuts. Sometime in the last few years, the island went from low-key retreat to party central. But post-Labor Day, the isle resets to its original pleasures, like bucolic beaches and accessible first-rate restaurants.

Stay at: 21 Broad grants you Downtown walking access and an autumn-ready fire pit out back. The Nantucket Hotel & Resort fully embraces the season with fire pit fondue, a hot cocktail hour, and an inviting hot tub.

What to do: Bike to Siasconset Beach , then call for reservations at Straight Wharf or Topper’s without fear of being laughed at. Do the indoor things you’d never bother with in summer, like catch a movie at Starlight Theatre, or peruse the Shipwreck & Lifesaving Museum and Whaling Museum. Instagram the Sankaty Head Light against a fall sunset. .



The entirety of the Cape is a revelation in fall: relatively sane bridge traffic and normal pedestrian traffic. And P-town is the peak of the off-peak destinations: the restaurants and bars are accessible, the shop owners can stop and chat, and the dunes are gorgeous in the autumn light.

Stay at: Now’s the time to rent that waterside Airbnb cottage you can’t even pretend to swing in July.

What to do: Plan a visit around Cape Cod Restaurant Week, or just book a last-minute table at Jimmy’s HideAway and then brag about it online. Check out the fall lineup at the Provincetown Theater (the Tennessee Williams Festival, who knew?). Start sewing your costume for Spooky Bear Weekend. Drive down the coast to the Vinegrass Music Festival on October 2nd.

Martha’s Vineyard

marthas-vineyardFLICKR/BEN PHILABAUM

Martha’s Vineyard
The Aquinnah sunsets are phenomenal this time of year, and this place is also seriously quiet in the fall. Year-rounders exhale and take some time to smell the flowers, and the biking views are genuinely gorgeous — all rolling hills and burnt-ember foliage.

Stay at: Two of the island’s newest and nicest hotels — Summercamp and The Christopher — are open until the end of October!

What to do: Throw your rod in the ring for The Derby, or celebrate the catches of those that do. Drink like a Desperate Housewife at the Food & Wine Festival.  If you’re around in November, take any and every opportunity to gorge yourself on in-season bay scallops.



Fall foliage starts north and creeps south, which means your earliest doses of crimson leaf tides are happening in Maine, so you can hit up both Kennebunk and Kennebunkport early for that double New England whammy: waterside leaf-peeping. Plus, The Clam Shack stays open until mid-October, when the lines become considerably less terrible than they are mid-summer.

Stay at: The entire Kennebunkport Resort Collection, including the lovely Tides Beach Club, lowers its prices considerably and offers a third night free on a two-night stay at all of its hotels.

What to do: Drive along Goose Rocks Beach and hike the Eastern Trail in Arundel. It’s probably time to start fasting for Coastal Maine Restaurant Week (October 21st-28th), and get super seasonal at the Kennebunk HarvestFest. Day-drink at David’s KPT–inside The Boathouse–while gazing out at the water.



It’s fall in Vermont, folks. It doesn’t get any better than that.

Stay at: Indulge in fireside tubs and fireplace butlers at Edson Hill. Stowe Mountain Lodge keeps its heated pool open all year round (hot tubs too), and can set you up on a ziplining trip through the fall foliage.

What to do: Splurge for dinner at Hen of the Woods in Waterbury, one of the best restaurants in New England, and drink under the leaves at Idletyme Brewing’s outdoor bar. You can sample dry hard cider in the Stowe Cider tasting room. Even if you don’t stay there, spa it up at Stowe Mountain Lodge — the lounge area offers really nice views of the nearby Mt. Mansfield.



Newport is another New England beauty that becomes far less lovely when you’re doing a conga line down the Cliff Walk. Once the masses dissipate, the whole area becomes better.

Stay at: The Attwater is the perfect city getaway: an urban boutique hotel just far enough removed from  Downtown. Or splurge for a night at Castle Hill Inn — the bonfire and s’mores continue through the end of September!

What to do: Enjoy the jazz brunch at Ocean House, laugh at boat shoes and lederhosen at the International Oktoberfest, or take a schooner cruise of the harbor. Take your last dip of the season at Easton’s Beach, then get fried clams at Flo’s. If you want the full Bowen’s Wharf experience, get drinks at Wharf Pub before dinner at Fluke.

Chebeague Island


Chebeague Island
There’s actually no bad time to escape to Chebeague, one of Maine’s loveliest islands, but September is definitely the island’s peak time. The summer crowds go away, and the foliage is already beginning to peek through. The crisp evenings are perfect for bonfires and s’mores, and best of all, the water is the warmest it will be all year!

Stay at: Chebeague Island Inn (open through October 15th) is the only game in town; good thing this grand hotel is one of the loveliest places you’ll stay in your lifetime!

What to do: Bike the circumference of the island. Grab lunch at the Ebb & Thyme Bakery & Cafe, and make sure you walk over to Little Chebeague island when the tide is out. Take a late-afternoon dip at Hamilton Beach when the tide comes back in . End the getaway by savoring the surf and turf at the inn’s award-winning restaurant!



What? Yes, we’re talking staycay, because Boston is actually pretty amazing in the fall, but sometimes you have to approach it like an outsider to appreciate its gifts.

Stay at: The Boston Harbor Hotel is one of those constants we take for granted:  a waterside locale combined with amenities like in-room bartending services. The Envoy is another great choice — nautically styled rooms, water views, and rooftop bar. And if you’re craving a deep autumn experience, the fireplace butlers at the Taj Boston are at your service!

What to do: Check out the Boston Calendar for daily events — everything from free movie nights to fluff festivals!


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