Whether it’s coffee or beer, “brews” always pair well with a bike ride. The Berkshires of Western Massachusetts is loaded with craft breweries, coffee shops and country roads. Put it all together and you have a perfect weekend adventure.
The back roads of the southern Berkshires provide for idyllic riding, and there are many routes to choose from. I love the variety of routes on Ride With GPS, along with the ability to create your own ride. An excellent resource for cycling routes in the Berkshires is Housatonic Heritage. Their suggestions for scenic rides can be found on Ride With GPS, and they provide maps if you prefer not to use a GPS.
Now let’s get to the brews- I organized these by town, so you can use each town as your jumping off point, destination or mid-point. I’ve also provided a suggested ride.
Table of Contents
Sheffield
Conveniently, the suggested ride provides easy access to these coffee shops and breweries. There’s even a nearby winery and distillery, if those are more your style.
- Bakin’ Bakery– As the clever name might suggest, the name of this bakery is derived from the pastry chef’s signature of using bacon to flavor a few of their signature treats. The bakery serves freshly brewed coffee, and the cinnamon role topped with icing, bacon and pecans will provide lots of quick burning carbs to kick off your ride, or save it for a mid-ride snack. Just don’t eat the whole thing at once. That’s a few too many calories for a bike ride. A few bites is enough- share it with a friend or two.
- The Marketplace Kitchen and Cafe– Kick off the day with a breakfast sandwich and espresso from this popular local cafe. Marketplace has a few locations in the area, including Great Barrington, so their healthy options are easy to find.
- Big Elm Brewing– Solar powered brewing is picking up steam in New England. Following in the footsteps of the Barrington Brewery, Big Elm is moving to solar power. Stop by the tasting room for a flight of their varied selection of inventive beers. I loved the refreshing 413 Farmhouse Saison and the classic West Coast IPA.
- Berkshire Mountain Distillers– Ever wondered what whiskey distilled from Big Elm beer might taste like? You’ll soon know. Try a tasting flight of whiskey distilled from various regional craft brews. The distillery has just about every style of gin imaginable. Pick up a bottle of their award winning Greylock Gin to take home for a refreshing gin and tonic.
- Sunset Meadow Vineyards– New England is quietly and quickly becoming a winemaking hotspot. Whether its wine, beer or food, I love coming across local producers and growers practicing sustainability. You’ll find local and sustainably grown wines at this tasting room. Stop by for a tasting or glass of wine made with grapes grown in their Connecticut vineyard, just 30 miles away.
Suggested Ride- Berkshire Bike Routes- Sheffield
Great Barrington
Great Barrington has a vibrant downtown and several coffee shops that are perfect for kicking off your ride. You’ll also find one of the Berkshires’ most popular breweries. If that’s not enough, the team at Berkshire Bike and Board, just outside of downtown can help with all your bike shop needs. Check their website for a list for great road, gravel and mountain bike ride routes.
- Barrington Brewery– Enjoy the signature Hopland Pale Ale from this solar powered brewery, along with their scratch made food. Try the house-made veggie burger, grass fed burger or smoked salmon salad.
- The Miller– Relax on the outdoor patio and enjoy a wide selection of craft beers from Northeastern breweries at this Main Street pub. Don’t worry, they also serve PBR if you really need to quench your thirst.
- Coffee- There are lots of options downtown, and you can’t go wrong. A few to try- Twoflower Cafe, Rubi’s Coffee and Sandwiches and Patisserie Lenox. Though they don’t serve coffee, it’s worth taking the time to try Extra Special Teas. It’s a non-profit cafe that provides a safe space for young adults with special needs to enter the workforce. They have every tea imaginable and some really creative blends.
Suggested Ride- Great Barrington Loop or Just the Alford Loop
Stockbridge
The former home of Norman Rockwell and the inspiration for many of his paintings, Stockbridge is one of my favorite towns in the Berkshires. You can use the historic Red Lion Inn as a jumping off point or relax on the porch and spend the night to recharge your tired legs.
- No 6 Depot– This roasters and cafe will soon become one of your go-to coffee shops. They buy high quality, sustainably produced beans for roasting and have fresh, healthy breakfast and lunch options. The homemade muffins will give you a quick energy boost in the middle of a long ride. Banana Nutella muffin, anyone?
- The Lost Lamb– You can’t help but smile at this cute french bakery, or patisserie, as you enter and see the multi-colored macrons and flaky pastries that pair perfectly with coffee and cappuccino.
Suggested Ride- Stockbridge from Town Hall or Sheffield to W. Stockbridge
Southfield
This small town is great to use as a destination/ turning point for your ride. Use Sheffield or Great Barrington as your starting points. The Southfield Store can serve as your rest stop to enjoy one of their lunch options and/or coffee and homemade baked goods. Create your own route to the store or use the suggested route, courtesy of Berkshire Bike and Board.
Suggested Ride- Ride to Southfield Store
