Note: These are last years routes. This year's routes will be added once they are solidified.
If all you are looking for is route links without descriptions, go to our RideWithGPS 2019 State Bike Tour Event Page
Note that if there are any days where the routes seem too difficult for you, we offer our participants “head start, drop off” service so you can start up to 20 miles into any ride. You can also choose to take a rest day on Saturday, Sunday or Tuesday.
Each day, choose from the Regular Route, generally 30 to 45 miles (but all are hilly) and the Challenging Route, between 55 and 70 miles, and may include more challenging climbs (Mt. Greylock, anyone?) Or do your own thing.
On “stay put” days (Saturday, Sunday, and Tuesday), you don’t even have to ride. We are staying in places where attractions are nearby or a short bike ride away.
Friday, we gather in Great Barrington, a clear favorite of Cycle Massachusetts “alumni”. We’re staying at Ski Butternut near East Mountain State Forest where the Appalachian Trail crosses. Set up camp and meet up with old friends and make new friends to ride with. We’ll be here all weekend. Check out the many food and drink options in Great Barrington including brew pubs, homemade ice cream, and lots more. Also, we’ll offer an optional short group ride (10-15 miles) late afternoon to warm up for the weekend.
Each day, choose from two great routes. Here’s a peak at what we are planning, along with points of interest to pique your interest and help you start dreaming about and planning your vacation.
Regular Route: Great Barrington – Hartsville – Monterey – Tyringham – South Lee – Stockbridge – Housatonic ~33 mi ~2100’
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This ride first passes by the Berkshire Fish Hatchery in Hartsville and continues to Monterey, where you can step back in time at the Monterey General Store. Or stop for a swim at Lake Garfield before a dramatic descent into the bucolic Tyringham Valley.
Riding through South Lee, and onto Rt. 102 you come into Stockbridge which features many attractions including the Norman Rockwell Museum; Chesterwood, the summer estate and studio of American sculptor Daniel Chester French; Naumkeag, a Gilded Age estate renowned for its gardens and rare Berkshire “Cottage”; and Berkshire Botanical Garden, a feast for the senses. Plenty of lunch options! Poke around to find “Alice’s Restaurant”.
Then bike along one of the most scenic stretches in the southern Berkshires along the Housatonic River through the tiny, picturesque village of Housatonic with its old mill buildings. If you skipped lunch in Stockbridge, how about the Berkshire Mountain Bakery, a short detour across the river over to Route 183. Return via the Guthrie Center (the former church where Alice lived and made famous by Arlo Guthrie) where you can stop in and have a look around. From here, it’s a short way back to Great Barrington.
Challenging Route: Great Barrington – Hartsville – Mill River – Southfield – New Marlborough – Sandisfield – West Otis – Tyringham – South Lee – Stockbridge – Housatonic ~56 mi ~3850’
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The Challenging Route offers some of the most pristine sections in the Berkshires. It diverges in Hartsville and continues down to the small village of Mill River where there is a rolling waterfall that descends over rock ledges. Visit the quaint Mill River General Store. From here, make your way to the Clayton-Mill River Road. Don’t go too fast, or else you’ll miss Umpachene Falls. Ready for a swim?
From here, it’s a short way to New Marlborough and then Sandisfield. Head north to West Otis on a beautiful, peaceful, wooded road with breath-taking views. Continue to the hamlet of Tyringham, joining the Regular Route up through Stockbridge and beyond.
Regular Route: Great Barrington – Sheffield – Mill River – Clayton – Canaan, CT – Ashley Falls ~40 mi ~1600’
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This route skips the climb up to Mt. Everett and New York State. It starts out with the Challenging Route to South Egremont, then heads down through Sheffield to Mill River by the Mill River General Store where you can step back in time. Cruise on a bit further south to Umpachene Falls – swimming allowed! This route goes down into Connecticut with pretty views along the southern Berkshires, and rejoins the Challenging Route on the return north near Ashley Falls, up through Sheffield to Great Barrington past the Covered Bridge (rest stop!), Shay’s Rebellion Monument, and W.E.B. DuBois homestead.
Great Barrington – South Egremont – Mount Washington – Copake Falls (NY) – Millerton (NY) – Lakeville (CT) – Salisbury (CT) – Ashley Falls – Sheffield ~60 mi ~3600’
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Start out through Great Barrington and ride through South Egremont to the tiny hamlet Mt. Washington (easy to miss, as there’s nothing there). We go by Mt. Everett. At 2625 feet, it’s not the highest in the state, but a formidable mass defining the southern Berkshires. And your legs will start to feel it by now. After all that climbing, it’s a thrilling descent past Bash Bish Falls (slow down so you don’t miss it!) into Copake Falls and Taconic Park in New York State. From here, beautiful views of the Hudson River Valley all along Route 22 south to Undermountain Road. Then it’s toward Millerton. From here, the ride goes east into Lakeville and Salisbury, Connecticut. Then it’s back home to Massachusetts through Ashley Falls and Sheffield to Great Barrington. Check out the Covered Bridge and the site of the bizarre UFO Monument on the return, and the Shay’s Rebellion Monument and the W.E.B. DuBois homestead.
Regular Route: Great Barrington – North Egremont – Austerlitz, NY – Canaan, NY – Hancock – Pittsfield ~33 mi ~2700’
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Monday is move day! Both routes take us into the Taconic hills of eastern New York State. Sleepy rural towns, rolling hills and scenic valleys, quirky museums, and charming farm shops. Here a “Kill” is a cool creek, not an agonizing hill. Stop in at the Austerlitz Historical Society. We ride into the hills above the Upper Hudson River Valley with lovely views, before returning into Massachusetts to Bousquet Ski Area in Pittsfield where we’ll be staying.
Challenging Route: Great Barrington – North Egremont – Austerlitz, NY– Ghent, NY – Chatham, NY – Canaan, NY – Hancock – Pittsfield ~66 mi ~4200’
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The Challenging Route follows the Regular Route to the Taconic hills of New York through Austerlitz, then diverges and follows a longer and more challenging route to even more adventure in this Dutch and Mennonite influenced valley. Stop by Art Omni, an open-air sculpture park – free, and open to the public! Say “OK” to this ride and you will ride by Old Kinderhook’s estate (President Martin van Buren) and Stuyvesant Falls before rejoining the Regular Route to head north through Chatham and Canaan to Pittsfield.
Regular Route: Pittsfield – Lanesborough – Cheshire – Adams ~47 mi 2700’
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Both routes start out toward and through Pittsfield State Forest. Balance Rock is a, adding a mile. Then pop out to Lanesborough where the Challenging Route diverges. Back roads paralleling the main road are more lightly traveled and scenic, going through Cheshire and the village of Cheshire Harbor, eventually taking you to the town of Adams right on the Hoosac River. Stunning views of Mt. Greylock dominate. The Visitor Center offers a great spot to relax. Lunch time? The Susan B. Anthony Birthplace Museum is a short side trip. We return on the beloved 11-mile Ashuwillticook Rail Trail, ending at the Berkshire Mall. From here, it’s back through Pittsfield.
Challenging Route: Pittsfield – Lanesborough – North Adams – Adams – Cheshire ~63 mi 4800’
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Mount Greylock is the one of the best cycling destinations in the whole state. At 3,491 feet, it is the highest point in Massachusetts, making the ascent challenging, and the descent demanding care and attention. But first, the Challenging Route starts out with the Regular Route until Lanesborough. From Lanesborough, we ascend the 10-mile Rockwell Road with several scenic vistas on the way up. At the top, climb the tower for a 360 panoramic view of four states. Then it’s a steep descent (caution!) into North Adams via Notch Road and Reservoir Road.
North Adams boasts the Mass MOCA (Museum of Contemporary Art) where you might spend some time. Another highly recommended side trip is the little-known Natural Bridge State Park, a hidden geological gem.
From here, we head back south on back roads to Adams, passing the Susan B. Anthony Birthplace Museum (closed Tuesdays, but you can stop and look around the grounds). Then we go by the Adams Visitors Center where we pick up the Ashuwillticook Rail Trail, rejoining the Regular Route.
Regular Route: Richmond – West Stockbridge – Alford – Great Barrington ~30 mi 2000’
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Wednesday is move day! The Regular Route is designed so you can return with time to spare or get on your way. We’ll be on rolling hills back through Richmond, West Stockbridge, and Alford, a few of the smaller, quieter towns in the Berkshires. Nonetheless, they offer great views, scenic and quiet roads, and we think you’ll like the route. Stop at Olivia’s Overlook for a view of the Stockbridge Bowl on the way into West Stockbridge. Visit a sculpture park in the village of West Stockbridge at Turn Park Art Space. Then it’s on down to Great Barrington through Alford. In Great Barrington, riders have the option to do a few more miles that includes a beautiful run along Valley Road, a quiet, wooded road with water views back to the start.
Challenging Route: Richmond – West Stockbridge – Alford – Great Barrington ~42 miles 3000’
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This is the same route as the Regular Route back to Ski Butternut, with an optional run up through the peaceful, wooded Monument Valley along a river and climb/descent of Blue Hill along Beartown State Forest and a fast cruise back down Route 23 to end your tour.