Road Trip Itinerary: New England Foliage

Roll down the windows and let that crisp autumn air come flowing inside — it’s the season for road tripping and leaf peeping in New England, the region of the United States that knows how to fête fall, above all. Get ready to enjoy a few days driving and discovering the coastal highlights of Rhode Island and Massachusetts before breaking inland for some of New England’s prettiest mountain views in the Berkshires, where the hillsides get carpeted with the hues of changing leaves.

Start In Newport, Rhode Island

Where To Stay: Club Wyndham Long Wharf, Club Wyndham Inn on Long Wharf, Club Wyndham Inn on the Harbor, Club Wyndham Newport Onshore, Club Wyndham Newport Overlook, Club Wyndham Bay Voyage Inn

Morning: Start the day enjoying sea breezes and coastal vies from the largest fort on the east coast, Fort Adams. It dates to the late-18th century and juts out into Newport Bay, with stunning views of the East Passage of Narragansett Bay. 

Afternoon: Stroll Newport’s gilded age history, past century-old homes, with a meander along the 3.5-mile Cliff Walk on the city's eastern shore. When the leaves are changing, the stately mansions here get bathed in a golden glow. Pack a picnic and stop to eat someplace along the Cliff Walk. Or drive 15 minutes west to Castle Hill Lighthouse. The lighthouse is built right into the cliff face and you can spread out your snacks with a view overlooking Narragansett Bay. 

Evening: The options are many for feasting on seafood in these parts. And wherever you dine, make sure you get a taste of Rhode Island’s famous calamari dish, loaded with zingy cherry peppers (it was designated the state’s official appetizer in 2014). One of the best versions of the spicy squid can be had at Brick Alley Pub & Restaurant, where you’ll also find 25 mostly-local beers on tap

Explore The Cape Cod Area

Where To Stay With RCI: The Edgewater Beach Resort #1877, The Soundings Seaside Resort #C788, The Breakers Resort #DC55, The Harwich Port #5008, Eastwood at Provincetown #5075 

Morning: On the hook of Massachusetts, Cape Cod brims with natural wonders — and the upper region is less than 2 hours away from Newport. Come fall, breathe in that crisp Atlantic Ocean air during a beach stroll at Cape Cod National Seashore, where 40 miles of undeveloped beach and marshland are protected and there are 11 hiking trails to explore. 

Afternoon: Mid-September marks the start of cranberry harvesting at the many bogs on Cape Cod, when the berries float to the water’s surface in a sea of crimson. You can head out on a tour in Harwich at the largest organic cranberry bog on the Cape to learn about the crop’s importance to the region while experiencing the colorful extravaganza set to a backdrop of changing fall leaves. 

Evening: Spend the afternoon strolling the atmospheric streets of Provincetown, popping into galleries, wine bars, and pubs to suit your fancy. If it’s lobster you’re craving, don't miss The Lobster Pot, a longtime local tradition that overlooks the harbor where you can try the crustaceans whole or as lobster arancini, egg rolls, and more.

End In The Berkshires

Where To Stay: Club Wyndham Bentley Brook

Morning: Drive four hours west of Cape Cod to the rolling mountains of the Berkshires, stopping off just before you reach Hancock in Lee, Massachusetts, to visit October Mountain State Forest. Here, you can catch the spectacle of the changing leaves along hiking trails within the state’s largest state forest (the Gorge Trail is a favorite). 

Afternoon: Visit the Hancock Shaker Museum where you can walk pathways, trails, and boardwalks through the living history of a former Shaker commune that was active here from the late 18th century until 1960. 

Evening: Just south of the Shaker village, the tasting room at Balderdash Cellars is open until 8 p.m. on Fridays and Saturdays and fronts a pretty lake. There’s often live music to enjoy while you sip on wines made from California grapes. Food isn’t served, but you're welcome to bring your own snacks for a BYO picnic onsite.