5 Fun Escapes Around New England to Make this Fall

INDEX

The Berkshires, MA | Chatham, MA | Portsmouth, NH | Southern Vermont | Sunapee, NH

Chatham, Massachusetts

Less-than-ideal forecasts should never cast doubt on a weekend jaunt to the Cape. By Kaitlyn Murray 

Nestled at the southeastern tip of the Cape, Chatham is the quintessential small-town seaside getaway. Via Getty Images/Halbergman.

A getaway to the cape is nearly synonymous with whiling away warm weather in the rolling sands and waves. Chatham, a beautiful oasis at the elbow of the flexed arm that makes up the beach-forward Massachusetts region, is especially prime for such activities. But what happens when those sun-soaked dreams are doused by showers? Keep reading for definitive proof that, rain or shine, there are plenty of ways you can have a perfectly lovely Cape escape.

THURSDAY AFTERNOON: Even at a meandering, languid pace, the drive from Providence to Chatham takes less than two hours. We pull up to the newly renovated Greyfinch Chatham Inn (greyfinchchatham.com) around 4 p.m. and are greeted with nautically inspired and spacious digs complete with an open concept kitchen, dining area and living area, as well as a master bedroom with an en suite bathroom. Forget a weekend; we could easily make ourselves at home for a week or two.

Greyfinch Chatham Inn provides a tranquil oasis for travelers. Photo courtesy of Cliff Brown and Cameron Hayes/Crown.

With a couple of hours to kill before dinner, we venture to the outdoor bistro area. We enjoy the giant Jenga and cornhole sets before soaking up the last of the evening’s rays on cozy lounge chairs by the pool.

THURSDAY EVENING: While the inn’s complimentary vintage bicycles are available and calling our names on the way out, our chic outfits dictate a quick car ride to dinner instead. We follow Main Street into the charming downtown, making note of which shops we want to visit tomorrow. We enter the Wild Goose Tavern (wildgoosetavern.com) at 6 p.m. sharp and are greeted warmly by the manager and host on our way into the classy dining room and out to the front porch for our picturesque al fresco experience. While the tavern is more refined than the name might suggest, its flavors are wildly delicious. Some Instagram stalking on the drive over reveals we can’t pass up the Goose fries — golden fries smothered in smoked Gouda, bacon bits and green onion — and we happily wash them down with a pair of refreshing, fruit-filled sangrias. We follow up with the lobster mac and cheese and the crisp clams casino flatbread and would probably lick our plates clean if it were socially acceptable.

Stop by the Wild Goose Tavern for lunch or dinner. Photo courtesy of Wild Goose Tavern.

With bellies full, but not stuffed enough to dissuade us from picking up a bottle of rose at the local liquor store, we head back to the inn. We return to the bistro area to enjoy a glass while figuring out plans for the next day by the fire pit, and then finally turn in for the night.

Indulge in the Gouda-and-bacon-loaded Goose fries at the Wild Goose Tavern. Photo courtesy of Wild Goose Tavern.

FRIDAY MORNING: The allure of the tucked away Snowy Owl Coffee Roasters (socoffee.co/espresso-bar-in-chatham) gets us up and out the door before 9 a.m. The tiny, trendy espresso bar serves up not just fancy caffeinated bevvies but also an array of sweet and savory pastries, plus locally sourced gifts like jewelry and apparel. We’re tempted to sip our iced lattes in the property’s courtyard, but the forecast’s promise of dwindling sunlight pushes us toward the ocean instead.

Stop by Snowy Owl Coffee Roasters to pick up your fuel for the day ahead. Courtesy of Snowy Owl Coffee Roasters.

Though it’s not technically our destination, we park across from the historic Chatham Lighthouse — don’t worry, we still admire its beauty with our phones — so we can walk down to the structure’s namesake: Chatham Lighthouse Beach (note: parking passes are required between June 23–Sept. 3). In another warmer and sunnier universe, we would be lounging here all day, but we manage to enjoy an hour of sinking our toes in the sand while breathing in the salty air all the same.

Chatham Lighthouse Beach is prime for swimming and scenic nature walks. Getty Images/Lagunatic Photo.

Not that we wouldn’t be getting plenty of the latter, anyway. A fifteen-minute drive brings us to Monomoy Island Excursions (monomoysealcruise.com) in Harwich Port for a ninety-minute seal tour around the barrier island of Monomoy. The cold and cloudy conditions have me skeptical that anyone, on land or sea, would be out and about that morning, but our boat is full of excited families and nature enthusiasts. The tour guides regale us with waterfront tours of local Chatham institutions and neighborhoods on our way out to Monomoy, where, of course, the highlight is finally coming across the many curious (and adorable) bobbing seal heads poking above the surface.

Catch glimpses of these cuties aboard the Monomoy Island Excursions’ seal cruise. Photo courtesy of Massachusetts office of Travel and Tourism.

FRIDAY AFTERNOON: Lucky for our rumbling stomachs, lunch options are already waiting for us right by the docks when we return. Though Dockside Cafe (docksidecafeharwichport.com) has regular restaurant service, we opt for its quicker walk-up window and get our fill of chouriço and clam chowder and fried codfish tacos.

Our initial plans included exploring the Monomoy National Wildlife Refuge (fws.gov/refuge/monomoy), known for its eight miles of protected sand, dune and marsh habitats, but the rain won’t let up (there’s always next time!). Instead, we return to Main Street for a bit of retail therapy. The shopping is reminiscent of Thames Street in Newport, where clothing boutiques, specialty shops and even the odd national brand like FatFace dapple the way. My personal favorites include Ducks in the Window (Love Batman? Ruth Bader Ginsburg? Construction? They’ve got a rubber ducky for that.), Jaks Chatham (I found my new favorite crewneck among its shelves) and the Squire Shop (more on that later). (ducksinthewindow.com, dflax.com/chatham_c_30.html, chathamsquireshop.com).

Chatham Lighthouse Beach. Via Getty images/JZ Hunt. 

FRIDAY EVENING: We stop back at the inn to change (read: forgo our sea-sprayed attire), then head back out for a cheap and casual bite from Mom and Pops Burgers (momandpopschatham.com). I am caught between the El Dyablo cheeseburger and the buttermilk fried chicken sandwich at first, but the jalapeno-topped beef won out (or lost, depending on how you look at it) in the end.

It wouldn’t be a true Cape getaway without an ice cream stop. While there are plenty from which to choose, we are most intrigued by Short ’n’ Sweet (facebook.com/shortnsweetchatham), a big yellow house-like building we passed earlier in the day. Delightfully old school with cash-only registers and chalkboard menus, employees let us sample a few flavors like the coffee Kahlua brownie, but my friend and I ultimately settle on Oreo and black raspberry, respectfully. We enjoy our sweet selections in the attached seating area surrounded by quirky memorabilia and throwback tunes from the jukebox.

There’s just one more stop to make. While shopping on Main earlier, we had stumbled upon the Squire Shop, a supplemental gift shop to the Chatham Squire (thesquire.com) across the street. Its license plate-themed merch has us intrigued, to say the least. Though the Squire has an expansive dining room, we quickly realize the tavern is clearly the place to be on a Friday night. We miraculously snag seats at the bar and take in the walls studded with license plates from all over the East Coast and beyond (though, suspiciously, I cannot find a single Rhode Island plate). The beer selection is worth writing home about (it redeems itself by having Narragansett on draft) and the rotating lineup on the calendar of events, like karaoke and trivia, entices us enough to return sometime during the week. We mingle with fellow tourists and friendly locals alike until it’s time to call it a night.

SATURDAY MORNING: Time to get back to reality, but not before hitting one last place on Main. After checking out around 10 a.m., Chatham Cookware (chathamcookware.com) is waiting and ready with nitro cold brews and hearty egg and cheese options sandwiched between Portuguese muffins to fuel our drive back. We may also make a detour to Devil’s Purse Brewing Company (devilspurse.com) for a pint. When it rains, you might as well let it pour, right?

NUTS & BOLTS 

Travel Time:  One-hour-and-forty-five-minute drive from Providence.

Miles: 93 miles.

How to Get There: I-95 and US-6 E.

Best Season to Go: Summer and fall, otherwise you may run into seasonal closures.

Bucket List for Next Time: Beachin’ it up and exploring the Monomoy National Wildlife Refuge.

Worth a Detour: Give into the temptation and stop by Devil’s Purse Brewing Company in South Dennis either on the way there or the way back. On Sept. 23, head to East Falmouth for the Cape Cod Brew Festival and taste the area’s finest.

Hopheads convene at the annual Cape Cod Brew Festival. Via Massachusetts Office of Travel and Tourism.

INDEX

The Berkshires, MA | Chatham, MA | Portsmouth, NH | Southern Vermont | Sunapee, NH