Head Out Of Boston For These Scenic Road Trips

You could use a break.

Nantucket, Massachusetts | Bokic Bojan/Shutterstock
Nantucket, Massachusetts | Bokic Bojan/Shutterstock

Safe to say we could all do with a departure from reality right now; alas, fleeing to a remote island nation isn’t exactly in the cards. But a well-planned road trip to get the hell out of dodge could be just what your sanity ordered. We’ve rounded up some of our favorite weekend off-season getaways, with updated suggestions for the Neverending Pandemic Era. Just keep checking in on each state’s regulations, as case rates continue to head in the wrong direction, and bring all your warmest duds (we’re keeping you outside as much as possible).

Castle Hill Lighthouse
Castle Hill Lighthouse | Howard Sun/Shutterstock

Newport, Rhode Island

Distance from Boston: One hour, 30 minutes

We can’t guarantee that the Cliff Walk will be free of tourists, but come the off-season, the path is far emptier than usual. If visions of the narrow path still makes you nervous, simply roll down the car windows and take the 10-mile drive so as to gawk at real estate favorites like The Breakers and Rough Point mansions. It’s not the usual party scene at Gurney’s. But with primo sunset views (and two pet goats!), it’s still a terrific bet—and its COVID-19 protocols make a contact-free visit much easier. Or dip into your savings for a splurge at Castle Hill Inn, where the water views can’t be beat (alas, no more lawn dining, even for guests). The city has also created a list of hiking and walking suggestions, the better to explore the region and get your nature fix.
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Martha’s Vineyard

Distance from Boston: One hour, 30 minutes to Wood’s Hole and one-hour ferry ride

Extensive beach time and an Aquinnah sunset can cure all ails, even in the off-season.. Harbor View Hotel recently wrapped up renovations, has instituted extensive safety policies, and also affords you the ability to take safe daily walks on Lighthouse Beach. Commit to distancing in the water and rent a boat from Island Spirit Kayak (which prefers you call about off-season rentals) or reserve a pass to drink deep the barrier beach pleasures of Cape Poge Wildlife Refuge. There are 44 miles of refreshingly flat bike trails and, of course, extensive beach walks are a must, be it South Beach or Inkwell or Katama. Check this list of continually updated outdoor dining options—we suggest calling in an order for a breakfast sandwich from 7a Foods, an alfresco fish and chips lunch from The Net Result, and a dinner of shrimp and grits at The Newes from America.
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Idletyme Brewing Company | Idletyme Brewing Company

Stowe, Vermont

Distance from Boston: Three hours

Everyone coming into Vermont right now must quarantine for at least 14 days—BUT you have the option of getting a PCR test on or after day 7 of quarantine and ending it then (assuming you’re negative).It’s worth the hassle. Stowe is the perfect spot to discover the state during the colder-weather season, what with all its hiking, biking, and other outdoor pleasures. Bring bikes and explore the 5.3-mile Stowe Recreation Path. Splurge for dinner at Hen of the Woods in Waterbury, one of the best restaurants in New England—so just be sure to plan ahead with reservations. Drink and dine under the eaves at Idletyme Brewing’s outdoor lunch area (reservation only), or sample dry hard ciders galore at Stowe Cider.
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Nantucket, Massachusetts

Distance from Boston: 90-minute drive to Hyannis followed by one-hour ferry ride

Wide beaches and bike paths aplenty makes social distancing a breeze. Add in the many walking trails and picnicking spots, and you can totally make a sleepy weekend of it. The Nantucket Hotel and Resort is pulling out all the stops to make your visit safe and enjoyable, from private dining and prepacked beach picnics to a cornucopia of hot cocktails. 21 Broad and 76 Main are smaller in-town boutique hotels that allow you to bunk down with fewer people. Be sure to bring your own two wheels--most rental shops in town are closed for the season—and head to Bartlett’s Farm, your one-stop shop for curbside picnic provisions. Continue onto Siasconset Beach for some seal and wave gazing; with fewer people about, now is also prime time to do the Sconset Bluff Walk. The island is doing an outstanding job of tracking all remaining indoor and outdoor dining options, and we recommend booking the Seagrille and—if the timing works—American Season (open from November 24 to December 12). 
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Lenox, Massachusetts

Distance from Boston: Two hours

No Kripalu, no problem? Actually, it’s a huge problem -- we hate seeing these iconic attractions closed down. But when you plan your Berkshires visits around high-profile venues, it’s easy to forget about the region’s simpler pleasures. The still-vibrant foliage, the hiking spots galore, and the chill vibes make for a restorative sojourn. The Cranwell has been reborn as the Wyndhurst Manor and Club—its massive grounds make it easy to stroll outside without fear of close contact, and the hotel is happy to set you up with a maple syrup tasting, among other late-fall pleasures. The Mount is the ideal spot to take a nature walk or forest hike (and experience more real estate envy). And the Pleasant Valley Wildlife Sanctuary will soothe your soul with the sites of wetlands and the sounds of birdsong.
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Provincetown, Massachusetts

Distance from Boston: Two hours

Maybe in ordinary times, you would have spent a summer week or two in Provincetown. We say, time to make up for lost debauchery. The entirety of the Cape is a revelation in fall: sane bridge and pedestrian traffic, zero Bugaboo traffic. And P-town is the peak of the off-peak destinations, with enough guests houses and restaurants still open and accessible to make life feel almost normal. Warm up with a long beach stroll at Race Point or Herring Cove, then snag a last-minute table at Jimmy’s Hideaway (the restaurant is keeping doors and windows open for ventilation) or Ross Grill (outdoor seating dependent on the weather). After waking up the next day and snagging breakfast sandwiches and lattes to-go from Relish (pre-ordering us a must), drive down 6A to Truro Vineyards and South Hollow Spirits, which is still open and humming. 
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Portland, Maine

Distance from Boston: Two hours 

There’s never a bad time to head to Portland, but it’s been a savior during the pandemic. (Look at it this way: Your chances of getting a plum restaurant reservation have gone up about 1,000%.) The Blind Tiger is a newly opened boutique gem, a converted mansion in the West End neighborhood that is currently offering weekly rentals. The Francis, another tiny boutique option, feels more like a stately home than a hotel (and will probably whet your Portland real estate lust). As for some dining faves that are still open for biz: hit up The Shop at Island Creek Oysters for bivalves and prosecco on tap (they’ve expanded their outdoor area), Chaval for seasonally inspired tapas (private rooms are available), and Novare Res Bier Cafe for drinks, where the heat lamps are cranking in the beer garden and it’s BYOB (bring your own blanket). The reopening of bars and tasting rooms has been delayed due to the state’s rising COVID-19 rates, so be sure to grab some takeaway cocktails and/or beers wherever you can.
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Meaghan Agnew is a contributor to Thrillist. You can follow her on Instagram.
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