Head Out Of Boston For These Scenic Road Trips

From the mountains to the Main Streets.

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

We could all use some good news these days. As it turns out, New England is in much better shape than any other region in the country when it comes to cases of COVID-19 and is taking precautions to stay that way. Local lawmakers are being hyper-vigilant, hotels have introduced extensive measures to protect visitors -- including flexible cancellation policies -- and outdoor museums and parks are reminding visitors to slow down and enjoy the simpler things in life. In fact, a well-planned road trip to get back in touch with nature could be the reprieve you didn’t know you needed. We’ve rounded up some of our favorite weekend getaways and updated suggestions for the 2020 era. Just please, read the fine print: Vermont and Maine in particular have strict guidelines as to who can and cannot visit.

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 the reports coming back say 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 Newport’s only outdoor pool and 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, which has reintroduced outdoor dining on the lawn for its guests. A schooner cruise of the harbor is once again possible, and a refined way to spend an afternoon. Or take some surfing lessons in nearby Narragansett with Warm Wind -- surfing is actually one of the safest outdoor activities to engage in right now. The city has also created a list of hiking and walking suggestions, the better to explore the region and get your nature fix.

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. 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. The Summercamp and The Christopher are both boutique seasonal spots that offer unpretentious stays. Commit to distancing in the water and rent a boat from Island Spirit Kayak 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 beaching is 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 entree of seared halibut on The Aquinnah Shop’s back patio.


Kennebunkport, Maine

Distance from Boston: One hour, 30 minutes

As a Massachusetts resident, you can only travel to Maine if you can quarantine for 14 days or if you’ve received a negative COVID-19 test in the last 72 hours. A challenge on multiple levels, to be sure, but Maine will be waiting for you all summer long. Sandy Pines Campground is now open through mid-October and has instituted a ramped-up cleaning program. For indoor folks, the intimate Captain Fairfield Inn bed and breakfast is now offering weekly rentals. Drive Goose Rocks Road starting at the Log Cabin Road side for some carside shore-peeping, then hit the actual Goose Rocks Beach. Walk through the Rachel Carson National Wildlife Refuge, one of the most calming spots we’ve visited in the entire state. Afterwards, enjoy an early alfresco dinner at The Tides Beach Club, which reopened on July 1. Get your lobster roll fix at The Clam Shack, which is taking online orders for pickup.

Idletyme Brewing Company | Idletyme Brewing Company

Stowe, Vermont

Distance from Boston: Three hours

The only folks who can travel to Vermont quarantine-free are those hailing from a county with less than 400 active cases of COVID-19 per one million residents, and only a few counties in Massachusetts can claim that status right now. So check out your county’s current situation here before booking. It’s worth the hassle. Stowe is the perfect spot to discover the state during the warm-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 -- the patio is tiny, so just be sure to plan ahead with reservations. Drink and dine under the eaves at Idletyme Brewing’s outdoor lunch area (reservation only). You can sample dry hard ciders galore while listening to live music on the Stowe Cider lawn, or carefully hit up the Stowe Farmers’ Market (you can preorder your goods online). A drive through Smugglers Notch actually seems like a great idea this summer, as does a hike down Mt. Mansfield after a gondola ride up and a stop at The Waffle.

Truro, Massachusetts

Distance from Boston: Two hours

Maybe you’d ordinarily be heading to Provincetown this summer, but the cancellation of all theme weeks has left you askew. Time to explore P-town’s sleepier next door neighbor and all its natural pleasures. Head of the Meadow Beach, part of the National Seashore, is a beautiful, wide, Atlantic-side beach -- and the entrance fees have been waived for the season. Or scoot over to the other side of the peninsula for the calmer, warmer waters at Corn HIll Beach (you need to pay a $15 entrance fee). Truro Vineyards and South Hollow Spirits is open and humming, allowing 90-minute visits and disinfecting all tables and chairs in between visits -- plus, the Crush Pad food truck is also open for lunch orders. In nearby Wellfleet, Mac’s on the Pier is the ideal spot for some oysters and a steamed lobster -- folks are taking their to-go orders and eating right on the beach.

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 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 socially distanced pool seating setups. 21 Broad and 76 Main are smaller in-town boutique hotels that allow you to bunk down with fewer people. Rent a sanitized bike from Nantucket Bike Shop and then 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 outdoor dining options, and we recommend booking outdoor reservations at Straight Wharf (a two-course, $75 alfresco dinner) and Cru.

Lenox, Massachusetts

Distance from Boston: Two hours

No Tanglewood, 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 these high-profile venues, it’s easy to forget about the region’s simpler pleasures. The blossoming 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 and literally just opened -- its massive grounds make it easy to stroll or read a book outside without fear of close contact. Hancock Shaker Village reopened earlier this month with one-way paths sanitizing stations and Ioka Valley Farm is still open and proffering its baby farm animals. The Mount has just reopened for self-guided tours and 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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Meaghan Agnew is a contributor to Thrillist. You can follow her on Instagram.