Find a Heaven for Biking and Craft Brews in Franklin County

For the best in cycling and sipping, all roads lead to this scenic corner of Massachusetts.

By Yankee Editors

May 21 2023


A key fundraiser for the Franklin Land Trust, the annual Deerfield Dirt-Road Randonnée offers a range of courses that can accommodate novices as well as the world’s strongest riders.

Photo Credit : Ben Barnhart / Franklin Land Trust

By Brion O’Connor; sponsored by the Franklin County Chamber of Commerce

No matter what kind of two-wheeled adventures they prefer, many cyclists will tell you that few things cap off an exhilarating day of pedaling quite like relaxing with a local craft beverage — especially when both are done in scenic surroundings. All that makes Franklin County an irresistible destination for bikers: Amid the hills and valleys of this rural enclave in northwestern Massachusetts, known for its natural beauty and historic small towns, there are memorable rides and myriad breweries and cideries to discover all along the way.

Long prized by farmers, the tranquil, rolling landscape of Franklin County also is a favorite backdrop for visiting cyclists.
Photo Credit : Recorder/Paul Franz/Massachusetts Office of Travel and Tourism

Nowhere is that enticing combination better represented than the Deerfield Dirt-Road Randonnée, or simply the D2R2, a famed gravel ride held in August that celebrates Franklin County’s “narrowest, oldest, twistiest, quietest, and most scenic roads” on routes that range from a gentle, 12-mile “family ride” to a legendary 180-kilometer challenge.

“Right after the ride, I take a dip in the river, change, and head right to the beer tent,” says D2R2 enthusiast Daniel Murphy of Hopkinton. “A good beer cannot possibly taste any better than after seven-plus hours of riding.” And Murphy has plenty of company: Founded by Saunders “Sandy” Whittlesey of Deerfield, the D2R2 has grown from a modest group ride in 1999 to a sanctioned event that draws more than 1,500 gravel enthusiasts to Franklin County each year.

A key fundraiser for the Franklin Land Trust, the annual Deerfield Dirt-Road Randonnée offers a range of cycling courses that can accommodate novices as well as the world’s best riders.
Photo Credit : Ben Barnhart / Franklin Land Trust

“Having grown up [in Maine] with the carriage roads of Acadia National Park in my backyard, the dirt roads of this region took me in immediately,” says Whittlesey. “Franklin County cycling is incredible for both its roads and its culture. Every other road is wonderful, and then you stumble into all kinds of interesting cultural spots: an art gallery in the middle of nowhere, the first schoolhouse ever to fly the American flag.”

The D2R2 offers an unforgettable overview of Franklin County’s beautiful landscape (fittingly, the event raises funds for the Franklin Land Trust), as well as a taste of the region’s top-notch craft brewing scene: Among the sponsors are South Deerfield’s Berkshire Brewing Company, known for such offerings as Steel Rail Extra Pale Ale and Berkshire Lager. But throughout the year, and across Franklin County’s 30-plus towns and villages, you can find endless ways to pair biking and craft beverages.

Biking Basics

One of the prettiest stretches of the Canalside Trail Bike Path runs along the Turners Falls Canal, which is crossed by several small bridges and flanked by a number of historic factories and mills. 
Photo Credit : Franklin County Chamber of Commerce

For road and gravel riders new to Franklin County, a terrific way to get your bearings is by taking a tour. Sunderland is home to two local companies, Adventure East and Frontier Cycling Tours, whose expert guides will lead you through small towns and down back roads on routes that deliver the most visual bang for the buck. Or, if you’re ready to strike out on your own, head to the Franklin County Chamber of Commerce website for maps of the Franklin County Bikeway. Its 240-mile network of road and off-road trails spans the entire county and includes options for all skill levels: from the easy 3.27-mile Canalside Trail Bike Path linking Turners Falls and Deerfield, to the Western Franklin County Loop, a scenic but challenging trek through the Berkshire foothills.

At Berkshire East Mountain Resort in Charlemont, downhill mountain biking enthusiasts can challenge themselves on a devilish array of man-made and natural jumps and obstacles at Thunder Mountain Bike Park.
Photo Credit : Douglas Mason/Berkshire East

If your cycling preferences lean toward the knobby tires of a mountain bike, you have plenty of options there, too. Sam Veggeberg, president of the Pioneer Valley Chapter of the New England Mountain Bike Association, suggests sampling the trail networks at Kenneth Dubuque Memorial State Forest in Hawley, Wendell State Forest in Millers Falls, and Deerfield River Trails in Charlemont. Northfield Mountain Recreation Area in Northfield, meanwhile, is an innovative collaboration with FirstLight Power Resources that not only houses a hydroelectric facility but offers 26 miles of family-friendly multi-use trails — there’s even a visitors center with restrooms.

Need more of an adrenaline rush? Thunder Mountain Bike Park at Berkshire East Mountain Resort in Charlemont features lift-service, gravity-enhanced downhill mountain biking. The park boasts 41 machine-built trails over roughly 25 miles, with more than 13,000 feet of total descent. Ratings range from beginner to expert (complete with man-made jumps and ramps); rental gear and lessons available, too.

Beverage Sampler

The L’Etoile family have been growing hops since 2008 on their Northfield farm, which also provides the romantic setting for The Brewery at Four Star Farms, which they opened in 2020.
Photo Credit : Franklin County Chamber of Commerce

As if by design, one of the most popular bike routes in this part of the Connecticut River Valley — the 18.7-mile River Road Loop — has a terminus near Berkshire Brewing Company in South Deerfield, which is open year-round with the added bonus of an outdoor beer garden during the warmer months. Another South Deerfield standout is the recently opened Tree House Brewing location, situated on roughly 50 wooded acres. In addition to serving up the brews that made this Massachusetts company a beer-world phenomenon, it sells wood-fired pizza and has stylish spaces indoors and out (including performance venues) for visitors to enjoy.

If you ride farther north, aiming for where the Connecticut River crosses the Massachusetts border, you’ll be within easy distance of another top beer oasis, The Brewery at Four Star Farms in Northfield. Lawn chairs and picnic tables beckon on the spacious lawn at this “farm-to-glass” operation, where you can take your pick from a full lineup of beers showcasing hops and grains grown on-site. More sudsy goodness can be found just one town over, in Bernardston, where the Hitchcock Brewing Company pours everything from light ales and lagers to dark porters and stouts, with an outside patio and live music making everything taste even better.

The distinct flavors of individual apple varieties — Baldwin, Cortland, Redfield, and more — inspire the sophisticated beverage offerings at West County Cider in Shelburne Falls.
Photo Credit : Franklin County Chamber of Commerce

Hard-cider enthusiasts, meanwhile, will quickly see why Franklin County is famous for that classic New England beverage. (This is, after all, the home of CiderDays, considered the region’s top annual celebration of apples and cider.) If you’re exploring the Franklin County Bikeway’s western routes, be sure to plan a stop at West County Cider in Shelburne Falls: Founded in 1984 by the Maloney family as one of the first small artisanal cideries in the U.S., it’s known for its creative, complex ciders as well as its expansive views, reaching all the way to the hills of Vermont and New Hampshire. More stunning views are on tap at New Salem Cider, set on a c. 1750 farm in eastern Franklin County, in the town of New Salem. Here, visitors can sample delicious small-batch ciders in the newly opened Cider Garden, which overlooks a century-old orchard and, in the distance, the Quabbin Reservoir.  

Long known for making superb sweet cider, New Salem Cider launched its own line of heritage hard cider in 2019 and also debuted a relaxing outdoor tasting space for sippers to enjoy.
Photo Credit : New Salem Cider on Facebook

Finally, for those who enjoy the fizz of fermentation without the alcohol, Artisan Beverage Cooperative in Greenfield has just the post-ride refresher you seek: Their Katalyst Kombucha comes in Concord grape, raspberry-lime, blueberry, and other zingy flavors. In the taproom they also offer alcoholic quaffs in the form of pre-Prohibition-style ginger beers and meads such as Green River Ambrosia.

Start planning your visit to Franklin County today, at