8 Most Bike-Friendly Towns in New England

What’s the point of a charming town if you can’t bike through it? New England has plenty of small towns where you can ride between cafés and historic sites without worrying about traffic or brutal climbs. Sandwiched between Canada, New York, and the Atlantic Ocean, the region is compact and features older infrastructure that makes biking a reasonable option. Some towns grew because of colleges, and some grew because of rivers or railroads, but every town has a common element: a master plan prioritizing people over cars. Whether you are biking to a trailhead, a bookstore, or a brewery, these towns keep everything close. If you’re curious to find flat roads, good food, and pretty scenery, then these eight towns are places to park the car and hop on a bike.

Brattleboro, Vermont

In Brattleboro, bicycles aren’t just common; they’re part of the town’s rhythm. This town in Vermont is flat, the neighborhoods are connected, and bike racks are located on nearly every corner downtown. Main Street, which has a slight hill, is lined with locally owned options such as Everyone’s Books, the Brattleboro Food Co-op, and Gallery in the Woods. Each of them is within a five-minute bike ride or walking distance of the others.

Just a short ride from downtown, Retreat Farm has 10 miles of trails and a seasonal food truck selection. You can also bike across the Creamery Covered Bridge, one of the oldest in Vermont.

Northampton, Massachusetts

This Massachusetts town is an ideal intersection of campus community and practical infrastructure. Paved bicycle lanes connect downtown to the neighborhoods, and the Manhan Rail Trail runs directly through to Easthampton. It’s also part of the larger New Haven and Northampton Canal Greenway, which connects with the Farmington Canal Heritage Trail, listed among New England’s top bike routes.

You can take the Manhan Rail Trail from the Smith College Museum of Art and ride past Amherst, then ride back downtown to Thornes Marketplace and Historic Northampton, all on greenway paths without needing to ride on streets with cars. It’s all connected, meaning you can bike to a rail-trail destination and still visit all the main spots back in town.

Hanover, New Hampshire

This college town thrives as much on bikes as on books. Due to the flat grid and compact size, it is easy to walk or ride a bike around Hanover. In just a few minutes, a cyclist can roll from Dartmouth Green to Baker-Berry Library and the Hood Museum of Art, all in the downtown loop.

You can pedal to Ledyard Canoe Club and have access to the river, or take the detour to Pine Park, a wooded preserve with bikeable trails. For extended rides, the Northern Rail Trail begins just south of here in Lebanon, offering over 50 miles of uninterrupted pathways through the wild.

Keene, New Hampshire

Few towns make biking feel as natural as Keene. The street grid is tight, the ground is flat, and you have the Cheshire Rail Trail running right through downtown. The trail will take you very near Central Square, where riders can stop at Prime Roast Coffee for a drink, browse indie titles at Toadstool Bookshop, or catch a show at the Colonial Theatre, a restored landmark from 1924.

From there, there is an easy ride to Robin Hood Park, which has wooded trails, a small lake, and plenty of space to picnic. The rail trail continues south from the park through scenic farmland and quiet wooded stretches.

Farmington, Maine

Here, bikes rule the backroads as well as the town center. In no time, you could be riding the route from Meetinghouse Park to the historic North Church, and looping around UMF’s Merrill Hall, built in 1863 and still utilized today. Most of the side streets connect these main points quickly without heavy traffic. You’ll spend less time braking and more time rolling.

Stop and get lunch at the Homestead Kitchen, Bar, and Bakery, a long-standing local establishment. It makes for a good stop midway through your ride, and since the streets connect well, you can cruise right to it. Then head out toward the Whistle Stop Trail, a packed-dirt pathway that meanders for nearly 15 miles to the nearby town of Jay, through woods, wetlands, and open fields.

Medfield, Massachusetts

Medfield trades car chaos for quiet pedals. The town’s peaceful neighborhoods and small downtown are perfect for leisurely cyclists. You can ride from Bellforge Arts Center, a former state hospital, to the Dwight-Derby House, one of America’s oldest homes, without even crossing a main road.

On Main Street, you can stop at the quaint independent shop Park Street Books or grab a snack at Noon Hill Grill. If you want to take a scenic break, you can bike up to Noon Hill Reservation, where you’ll find wooded paths and open vista views just a few minutes outside the town center.

Middlebury, Vermont

In Middlebury, everything worth seeing is just a ride away. The compact downtown is centered around Otter Creek, with bike access to Middlebury College and the Henry Sheldon Museum, the Town Hall Theater, Washington Street’s Retro Realm arcade, and the historic Frog Hollow Stone Mill, a 1840 grist mill now housing a market, event space, and hotel rooms.

If you’re in the mood for a picturesque loop, head east into East Middlebury and take on the Fern Lake to Middlebury Gap loop, which winds through forest and lake views before coming back around through quiet country roads to connect you back to Otter Creek.

Windsor, Vermont

Windsor blends historic charm with smooth, bike-friendly routes. Riding through the Windsor Village Historic District with 18th and 19th-century buildings up to the Old Constitution House, where Vermont declared independence in 1777, gives you two bikeable destinations with low traffic and short distances between stops.

You can pedal across the river to Artisans Park, a small complex with Harpoon Brewery, Simon Pearce Glassworks, SILO Distillery, and the Path of Life Sculpture Garden, all within walking distance of each other once you arrive. You can also ride around Lake Runnemede or along a looping riverside trail before rolling back downtown without a single hill to climb.

Where Cyclists Come First

You don’t have to live in a sprawling metropolis to embrace a bikeable lifestyle. These eight New England towns demonstrate how careful planning, flat roads, and density can go a long way. Whether it is a college green, a historic trail, or a riverside brewpub, everything worthwhile is close enough so you don’t need to drive. Less time stuck in traffic means more time enjoying the ride. When the roads feel safe and the stops feel rewarding, biking becomes more than exercise. It becomes how you experience the place. So pack your gear, pump your tires, and ride to a town where the bike lane isn’t an afterthought. In these towns, it is the main event.