Prepare to Be Enchanted: Bike Rides in New England to See the Fall Foliage

Ah, Fall in the Northeast. The months ending in R are here meaning the leaves are starting to change color, school is back in session and, of course, shellfish is at its peak.

What better way to see the best of New England than slow travel on two wheels? Below we propose two bike tours in each of the Northeastern States along with our lodging recommendation that brings out the true character of each locale. Prepare to be enchanted by these bike rides in New England!

Outer Cape, MA

Cape Cod by bike becomes all the sweeter as the off-season takes hold of Massachusetts’ lighthouse-speckled arm. Beaches and highways start to empty out and hotel prices, lucky for Fall visitors, see an immediate drop. trivago data shows that Provincetown hotel prices drop by 34% between August and September alone with a declining trend continuing into November.

Provincetown, the site of the first landfall for the early Pilgrims, is our branching point for covering Cape Cod by bike. The foodie epicenter of the Cape has more to offer between meal times: keep an eye out for one-of-a-kind shopping, theater shows and the city’s own LGBT enclave.

Short Route: Province Lands Bike Trail to Race Point beach (6.5 miles)

Climbing past Route 6, discover the northern-most point of Cape Cod along the Province Lands Bike Trail. Find your fuel for the day at Chach Restaurant on Shank Painter Rd. as you head out of Provincetown. The circular route through the NPS Cape Cod National Seashore criss-crosses sand dunes linking Race Point Beach in the north and Herring Cove Beach in the west.

Long Route: The Cape Cod Rail Trail to Nauset Beach (30 miles)

Take the 6A “upwind” (towards the mainland) until it joins up with Collins Road and Ocean View Drive. Where Ocean View meets Lecount Hollow Road, you’ll find the tip of the Cape Cod Rail Trail which sends you on a straight trajectory until a left turn towards the long sandy stretches of Nauset Beach. Hang a right just before the Route 6 underpass at Mile Marker 17 which will lead you directly to a plate of fresh-caught seafood at Arnold’s Lobster & Clam Bar.

Where to Park for the Night: Benchmark Inn

The keys to a former captain’s home have been handed over to the Benchmark Inn’s current Swiss owners Dan and Daniel who have transformed the Gallery District address into a cozy and cool bed & breakfast worthy of a week’s escape in Provincetown. Benefiting from an adults-only guest policy, imagine quieter moments as a couple in the Jacuzzi or during a relaxed breakfast on the patio.

With a 94/100 rating on trivago, the Benchmark Inn is one of our most-loved stays in Massachusetts. As a leading environmentally-conscious property, there is no better place to stay in Provincetown during your slow travel getaway.

Benchmark Inn

9.2 Excellent (1005 reviews)

Lake Champlain, VT

With Québec to the immediate north and New York State on its western edge, Lake Champlain marks the far northwest corner of New England’s reaches. This special corner of northern Vermont, also known for hometown ice cream heroes Ben & Jerry, should not be overlooked, much less in the Fall. Take in the warm hues of the Adirondacks while chomping into an in-season Vermont McIntosh apple – it doesn’t get much purer than that!

Luckily, Vermonters are avid bikers and the Lake Champlain area has no shortage of bike trails whether you’re on a mountain bike or road bike, going for an uphill challenge or trying to go the extra mile. There’s even the full 350-mile Lake Champlain bikeway that leads cyclists right into Canada for a quick bonjour and a well-deserved maple donut.

Short route: Trail Around Middlebury (16 miles)

This complete loop around the college town of Middlebury quickly takes trail riders off of Main Street and to the periphery of the town where you’ll pass fields of cows, the Otter Creek Gorge and the Middlebury College Campus. On your way back into town, why not end the TAM with a drink and a snack at the Woodchuck Cider House on Exchange St.? Twenty varieties of America’s beloved ciders are on tap including a seasonal apple pie-inspired Fall Harvest Cider.

Long route: Burlington to South Hero (41.5 miles)

Though a longer route than the TAM, taking the Island Line route to Grand Isle is a real treat with the Fall colors as your backdrop. Set out from the beginning of the trail in Oakledge Park south of Burlington and make your way up through the Downtown following the shore of Lake Champlain on your left. At Mile 12, things get interesting thanks to the Local Motion bike ferry which will sail you the 200 feet across the Colchester Causeway into South Hero! Don’t get around to the Island Line too late; the ferry operates only from May 26 to October 9.

Where to Park for the Night: Middlebury Inn


As a member of the Historic Hotels of America, you can bet that a stay at the Middlebury Inn is something out of the ordinary. Over the course of its history dating back to 1827, this boutique inn strives to maintain the integrity of the property – keeping defining features like its circular staircase and wrap-around veranda (perfect for a lazy rock-about after a day on the trails).

You may even be convinced that the Inn is straight out of an episode of Gilmore Girls. Meanwhile, WiFi, fitness passes and afternoon tea (all included in the room rate) make the deal all the sweeter!

Middlebury Inn

Top rated
8.8 Excellent (2081 reviews)

Casco Bay, ME

The 66,000 or so residents of Portland, Maine love their city just the way it is. Posed on a peninsula in Casco Bay, the small port city is the perfect size for a biking weekend in town and along the Atlantic coast. An unpretentious approach to business and life emanates throughout the city which only supports the city’s official slogan, “Yes. Life’s good here.”

A wander around the Old Port will set your inner shopaholic free in the cobble-stoned streets linking boutique after boutique. A picnic for your biking day trip? The Portland Public Market should stock your saddlebags with all of the provisions necessary.

Short route: Eastern Promenade and Peaks Island (7.3 miles)

Start the shorter of our two proposed Casco Bay routes by acquainting yourself with the East End of Portland. The Eastern Promenade occupies the entire northeastern edge of town opening onto views of Casco Bay and your next stop: Peaks Island.

At the Casco Bay Lines Ferry Terminal situated at the foot of Franklin Street, catch the boat to Peaks Island which will deliver you and your wheels to this 720-acre islet in just 15 minutes. Circumnavigate the island’s 4-mile coastal trail by sticking to Island and Seashore Avenues. Scoops of Gifford’s Ice Cream at Down Front are the perfect way to pass the time before catching the next ferry bound for the mainland.

Long route: Portland to Prouts Neck (39 miles)

Head due south of the downtown up and over the Casco Bay Bridge before linking up with Cottage Road and Shore Road in the direction of the landmark Portland Head Light. After snapping a few pics, retrace your tire tracks back towards the bridge before a left turn onto Highland Ave.

The tree-covered Eastern Trail will lead you towards Scarborough where a succulent Lobster Roll awaits on the outdoor patio at The Bait Shed. A ride to the tip of Prouts Neck, across the inlet from Scarborough, is worth the detour before taking your crustacean-loving self back to Portland.

Where to Park for the Night: The Danforth


Each of the well-appointed rooms at The Danforth takes its inspiration from a different Portland neighborhood. The Eastern Promenade room, whose original muse you can bike for yourself, incorporates subtle furnishings from the Far East standing alongside pieces from Maine artists and a toasty wood fireplace.

Guests are invited to make themselves at home around the Inn whether in the third-floor conservatory, the private gardens, the billiard room or the dining room during complimentary breakfast hours. The on-site Tempo Dulu restaurant lists a Southeast Asian Lobster tasting menu and a chef tasting menu inspired by a Dutch-Indonesian Rijstafel spread.

Blind Tiger Portland - Danforth Street

9.6 Excellent (251 reviews)

Merrimack Valley, NH

Once known for its cotton textiles, the Merrimack Valley continues to be one of the liveliest corners of New Hampshire. The Merrimack River starts north of the state capital of Concord, before passing through Manchester (the creative heart of New Hampshire) and finally to Nashua in the south.

In the Fall, the Merrimack Valley experiences the changing of the colors later than the rest of the state with peak foliage rolling through around Halloween. See Nashua for yourself on two wheels at this magical time of year.

Short Route: Nashua Canal Trail in Mine Falls Park (6 miles) — recommended for mountain bikes

Lose yourself in the tranquility of Nashua’s green escape, Mine Falls Park. The six-mile loop that wraps around the water features of Mine Falls is conquerable even by the most amateur of mountain bike riders. The focal point of the trail is undoubtedly the 36-foot falls which was created during the digging of the Nashua Canal in the 1800s. On the western tip, take a break at the Mine Falls Gatehouse which once served to control the flow of water to the on-site mill for cotton textile manufacturing.

Long Route: New Hampshire Heritage Trail around Manchester (14 miles)

Head out along the Piscataquog Trail which follows the similarly-named river into the Merrimack. Cross the pedestrian bridge to the opposite side of the Merrimack and cycle southward before turning around to head into Downtown Manchester.

Take a right at the Notre Dame Bridge and navigate your way up to Bridge Street. As you cross Beech Street, you may consider a visit to the Currier Museum of Art, Manchester’s premiere fine arts institution. Follow Bridge Street out to Candia Road for a spectacular ride along the Londonderry Turnpike with sweeping views of Massabesic Lake.

Alternatively, suburban shopping options are in no short supply along South Willow Street and at the Mall of New Hampshire. With zero sales tax across the State of New Hampshire, there is no better reason to shop till you drop!

Where to Park for the Night: The Bedford Village Inn


On the fringes of Manchester sits the quaint Bedford Village Inn. The destination inn is part of a ten-acre estate with four different dining options and a lavish Great Hall for larger celebrations.

Molton Brown toiletries posed in an Italian white marble shower. Hand-carved four-poster beds to collapse into. Whirlpool tubs to undo a day’s worth of knots. Furnishings that capture the essence of the Northeast – and the luxe list goes on. Not to be missed is the evening turndown service that includes the oh-so-sweet addition of homemade cookies.

Bedford Village Inn

Top rated
9.6 Excellent (626 reviews)

Newport County, RI

In spite of its miniature size, Rhode Island boasts 60 miles of bike paths radiating out of Providence and further south lining some of the State’s 400 miles of coastline encompassing Narragansett Bay. To capture the essence of a relaxing pumpkin-spice Fall, we’re leaving the bustle of Providence behind for Newport County on the State’s Atlantic front. See quintessential New England here for yourself through its piping hot clam chowders, larger-than-life mansions and coastal bike paths.

Short route: Ocean Drive (11 miles)

Experience the mesmerizing waterscapes for yourself, so impressive that New York’s elite circa the late 1800s couldn’t resist building their own summer cottages. The Ocean Drive by bike allows visitors to stop and admire the best of Newport’s summer cottages including Hammersmith Farm (Jackie Kennedy’s childhood home), The Breakers and The Marble House.

On the route’s east end, you may want to lock up your bikes to tackle the Cliff Walk on foot. By the end of this eleven-mile loop (when you reach the landmark Caste Hill Lighthouse), you might also be as convinced as a Vanderbilt to buy up property in this picturesque corner of Rhode Island.

Long route: Conanicut Island (20 miles)

Get a full impression of Newport’s western neighbor, Conanicut Island, by completing a round island tour from tip-to-tip. Catch the #64 bus across the Newport Bridge and disembark with your wheels at the Jamestown Ferry Landing. Narragansett Avenue is perfect for a pre-ride bite before setting out westward on Beavertail Road. At the end, you’ll find the island’s southern tip which has been guarded by the Beavertail Lighthouse since 1749.

Connect yourself to North Road, which will link you to the northern tip of island where the Conanicut Island Light’s turkey red siding has been a landmark for ferries crossing between Jamestown and Newport since 1886. Wes Anderson’s 2012 flick Moonrise Kingdom filmed on Conanicut including the Island Light and Watson Farm just outside of Jamestown.

Where to Park for the Night: The Almondy


Cyclists looking to immerse themselves in the history of Newport won’t have to look much further than the Victorian-style Almondy Inn in the city’s historic district. With just six suites, guests are sure to be well taken care of with added perks like the afternoon Wine & Cheese social.

The newly-renovated Captain’s Quarters occupies the third floor of the Inn, dividing its space between two bedrooms, a fully-appointed kitchen, two living spaces and a balcony looking onto Narragansett Bay. After a day cycling around Newport, we couldn’t think of a better way to unwind than a bit of Netflix & Chill courtesy of the Inn’s in-suite Smart TV hookup.

Almondy Inn

Top rated
9.8 Excellent (924 reviews)

Litchfield Hills, CT

When you picture New England in the autumn, it might resemble something like a fiery gradient of foliage, a white spired-topped church, evening strolls wrapped in fleece and homey B&Bs – and at any point in October and November, that is the exact scene playing out in the northwestern town of Litchfield Hills.

While the destination estate and spa Winvian Farm may have bumped Litchfield Hills onto the national travel bucket list, this romantic corner of CT still stays true to its quaint way of life with antique shops and a network of hiking trails. Roll through the hills and valleys of Connecticut’s northwest at this magical time of year – and you best be doing it on only two!

Short route: Litchfield to Bethlehem (19 miles)

Start your ride to Bethlehem by passing through the center of Litchfield to admire one of New England’s most photographed churches, the Litchfield First Congregational. Head south on the appropriately-named South Street before taking Webster Road to connect to Alain White Road. Pop by the camera-friendly grounds of Winvian Farm before continuing onto Bethlehem. If you’re lucky enough to pass through on the weekend of Oct 8th and 9th, check out the pungent Garlic & Harvest Festival at the local fairgrounds.

For lunch, try the Painted Pony for one of their eight different burgers. Ambitious cyclists can try the extra four-mile trip to the Abbey of Regina Laudis, a Benedictine order dedicated to monastic art with a shop open to the public.

Long route: Tour of Litchfield Hills (30 miles)

Following in the tire tracks of the annual Tour of the Litchfield Hills charity bike ride, this 30-mile loop out of Litchfield is the perfect circuit for taking in the warm hues of autumn in Northwestern Connecticut.

On your loop, don’t pass up a pitstop for some ‘single cow origin’ chocolates at Milk House Chocolates in Goshen if you’re passing through on a Thursday through Sunday. Set down your kickstands along Torrington’s Main Street which may present some interesting late afternoon shopping opportunities before returning to Litchfield.

Where to Park for the Night: The Litchfield Inn


The Litchfield Inn straddles the line between a B&B and a bona fide hotel by taking the best elements from both: individually-decorated rooms and attentive service matched with an in-house restaurant, fitness center, business center and library.

Each themed room at the Inn bears a different personality from the opulent Contessa to the fortified Cabin. Both a Jacuzzi suite and Jacuzzi room are available for visitors seeking some post-ride hydrotherapy. Complimentary bicycle rentals for Inn guests make touring Litchfield Hills dead simple.

The Litchfield Inn

Top rated
9.0 Excellent (1637 reviews)