5 Of The Most Scenic Leaf-Peeping Road Trips In New England

5 Of The Most Scenic Leaf-Peeping Road Trips In New ENgland

September 12 2019

According to a recent study by MMGY Global’s Portrait of the American Travelers (POAT), 2019 travelers have discovered a brand new form of a road-tripping, where travelers fly to a starting point and road trip from there.

This new segment of travelers, Wings & Wheels travelers, is being propelled by Millennial families seeking nostalgia and family bonding. Fifty-seven percent of Millennial families took road trips that began from another city, compared to just 41% of singles and 28% of couples.

Leaf-peeping in New England is the ultimate road trip. Create your own starting point at any airport where foliage is changing. Meanwhile, here are five samples of New England’s most lovely areas in fall.

Boston, Massachusetts 

You can stay in Boston, or make it a starting point before packing up the rental car and visiting other areas. Walk along tree-lined Commonwealth Avenue, where golden foliage forms a canopy. Explore the Public Garden and Boston Common, or opt for a scenic bike ride or picnic along the Charles River Esplanade.

On October 19 – 20, when the Head of the Charles regatta takes over the city, foliage begins to peak along the Charles River. Don’t miss the Arnold Arboretum, designed by the creator of NYC’s Central Park, where some trees smell like cotton candy when they turn. And travelers can tour Fenway Park in all of its glory during offseason.

  • How to Get Here: Fly into Boston Logan International Airport
  • When to Go: Columbus Day through mid-October
  • Where to Stay: The urban luxe Hotel Commonwealth, situated right on Commonwealth Ave., is just a quick stroll to the Public Garden, Boston Common and Cambridge.


Manchester, Vermont

At the foot of Mount Equinox in the Battenkill River Valley, Manchester is a quaint, postcard-perfect town. You can mega-shop at the Manchester Designer Outlets, dine at artisanal restaurants, and hike, bike, fly fish, off-road drive, kayak and more. Take a tour of Hildene, The Lincoln Family Home; and drive past Bromley and Stratton ski resorts, whose slopes are blanketed in color during the fall.

How to Get Here: VT Route 30

  • When to Go: Mid-September through early October
  • Where to Stay: Kimpton Taconic, a cozy New England hotel with views of the Taconic and Green Mountain ranges and locally made in-room walking sticks and complimentary bikes.


Burlington, Vermont

In the heart of the Green Mountain State, Burlington is on the edge of picturesque Lake Champlain. Take in the season’s foliage on a Bike & Brew Tour, at some of the top breweries and cider houses in the country. Or head to Shelbourne Farms, a sustainable 1,400-acre working farm, and indulge in cheddar cheeses from their herd of purebred Brown Swiss cows while watching the cheesemaking process firsthand.

Head to Brot Bakery for a breadmaking class with German-born now-Vermonter Heike Meyer, with classes like Rustic Country Breads or Artisan Baking: Delectable Pastries with Sourdough – Cakes, Croissants, Brioche and more.

How to Get Here: I-93 to I-89

  • When to Go: Mid-September through mid-October
  • Where to Stay: The locally-inspired and independently owned Hotel Vermont offers a wood burning fireplace and weekend cider/spirits samplings as soon as you enter. A top floor king has a whirlpool tub and in-room fireplace. Vermont Flannel robes and in-room hot toddies from the hotel’s Bedtime Menu will warm you up as well.


Kennebunkport, Maine

Enjoy sea breezes along with colorful foliage in this historic village straddling the Kennebunk River. Antiquing, kayaking, and eating lobster rolls are fave activities here.

Sail along the coast on the Schooner Eleanor, a 55-foot traditional gaff-rigged schooner that cruises the rugged foliage-lined coastline from Cape Arundel to Cape Porpoise. Or explore Kennebunkport by bike through tree-lined streets and foliage-covered pathways like the Eastern Trail along a gravel path.

How to Get Here: I-95

  • When to Go: Late October
  • Where to Stay: Kennebunkport Resort Collection’s year-round hotels offer diverse, luxury accommodations for travelers. Road-tripping adults will enjoy the upscale Cape Arundel Inn & Resort with ocean views.

The Kennebunkport Inn, is close to shops, restaurants and galleries. The Boathouse Waterfront Hotel has panoramic windows, private balconies and an expansive outdoor deck.


Rhode Island

You’ll need only a few days to experience the state. From the cultural capital of Providence, drive along the Ocean State’s coastline through South County. Check out how the Vanderbilts spent summers in Newport. Or take the road trip to the water by sailing away on the Block Island ferry, just 13-miles off the coast of Rhode Island.

How to Get Here: I-95

  • When to Go: Mid-October
  • Where to Stay: The Omni Providence Hotel is next to Providence Waterplace Park and Riverwalk. Ocean House provides guests with a beachfront view and unrivaled service. In Newport, stay in your very own gilded mansion at The Chanler at Cliff Walk, a short walk from all Newport’s famous mansions.


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