State Bike Tour Routes - Cycle Massachusetts

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State Bike Tour Routes

2019 Routes

Here are our route descriptions and draft routes for the 2019 tour. Please note, the routes are subject to change.

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.

Back by popular demand!

This year, Cycle Massachusetts returns to the beautiful, scenic, renowned Berkshires, summer home to millionaires of the Gilded Age. There’s no shortage of things to see and do here – besides cycling, that is. So much so that we think you’ll have trouble deciding what to do each day. Museums, hiking trails, music and theatre, wineries, breweries, and of course – challenging climbs (we’ll try to make as many optional as we can!)

Each day, choose from the Regular Route, generally 30 to 45 miles (but all are hilly) and the Challenging Route, between 55 and 75 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 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 a short group ride (20 miles or less) at 5 p.m. to warm up for the weekend.

Each day, we have two great rides to choose from. Here’s a peek at what we are thinking, along with points of interest to pique your interest and help you start dreaming about and planning your vacation.

NOTE: All routes are subject to change as continually review everything to ensure we have the best routes possible for you!

Saturday Routes

Regular Route: Great Barrington – Monterey – Tyringham – South Lee – Stockbridge – Housatonic ~34 mi ~2325’

Click for Saturday Regular Route

This ride first passes by Lake Buel and 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 Tyringham Valley.

Riding through South Lee, and onto Rt. 102, you come to 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? Return via the Guthrie Center (the former church where Alice lived which was made famous by Arlo Guthrie) where you can stop in and have a look around. From here, it’s a short ride back to Great Barrington.

Challenging Route: Great Barrington – Sheffield – Mill River – Southfield – New Marlborough – Sandisfield – West Otis – Tyringham – South Lee – Stockbridge – Housatonic ~60 mi ~3750’

Click for Saturday Challenging Route

The Challenging Route starts in the opposite direction toward Great Barrington and joins the Regular Route in Tyringham. It offers some of the most pristine sections in the Berkshires. After Great Barrington, the ride goes south through Sheffield, passing the oldest covered bridge in Massachusetts (look for the bizarre UFO monument nearby). The ride then turns east and from here, wonderful views of the Housatonic River greet you. You ride through the small village of Mill River where there is a roiling waterfall that descends over rock ledges. Visit the quaint Mill River General Store before you get to the park.

Make your way to the Clayton-Mill River Road, and when you see a bridge, you’ll turn right on a gravel road over the river you’ve been following. Just after this wooden bridge, turn right into Umpachene Falls Park. 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. Continue to the hamlet of Tyringham where you join the Regular Route.

Sunday Routes

Regular Route: Great Barrington – Sheffield – Mill River – Clayton – Canaan, CT – Ashley Falls ~40 mi ~1525’

Click for Sunday Regular Route

This route skips the climb up Mt. Everett and the excursion into New York State. It starts out with the Challenging Route but only as far as Great Barrington, then heads down to Mill River and Umpachene Falls (swimming allowed!). This route goes into Connecticut and rejoins the Challenging Route on the return near Ashley Falls, etc.

Challenging Route: Great Barrington – South Egremont – Mount Washington – Copake Falls (NY) – Millerton (NY) – Lakeville (CT) – Salisbury (CT) – Ashley Falls – Sheffield ~70 mi ~3800’

Click for Sunday Challenging Route

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. Optional climb on the summit road to the top? 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, we pick up the Harlem Valley Rail Trail four miles south to Undermountain Road. Then it’s toward Millerton. From here, the ride goes east into Lakeville, Connecticut. Then it’s back “home” to Massachusetts through Ashley Falls and Sheffield to Great Barrington.

Monday Routes

Regular Route – Great Barrington – Austerlitz, NY – Chatham, NY – Canaan, NY – Hancock ~43 mi ~2800’

Click for Monday Regular Route

Monday is move day! Both routes take us into the Taconic hills of eastern New York State. Bustling New York City? Fahgettaboudit – this is the other New York, with 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, and time seems to stop as we meander the New York byways before returning to the Massachusetts town of Hancock, near Pittsfield, where we’ll be staying. Stop in the Hancock Shaker Village to travel to another place and time and culture. The Shakers were known for their crafts, herbs, carpentry, and culinary skills.

Challenging Route – Stay Tuned

The Challenging Route will likely follow the Regular Route to the Taconic hills of New York, where we diverge and follow a longer and more challenging route to even more adventure in this Dutch and Mennonite influenced valley. Say “OK” to this ride and you will visit Old Kinderhook’s estate (President Martin van Buren) and Stuyvesant Falls before rejoining the Regular Route to head north through Chatham to Hancock.

Tuesday Routes

Regular Route: Pittsfield, Lanesborough, Cheshire, Adams ~45 mi 2415’

Click for Tuesday Regular Route

Both routes start out through neighborhood streets of Pittsfield. Optional side trips in Pittsfield State Forest include climbing Berry Mountain to Berry Pond early in the ride when your legs are fresh. Balance Rock is a second, shorter side trip, also in Pittsfield State Forest. Then we 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 away. We return on the beloved 11-mile Ashuwillticook Rail Trail, ending at the Berkshire Mall. From there, it’s back through Pittsfield to Hancock.

Challenging Route: Pittsfield, Lanesborough, North Adams. Adams, Cheshire ~70 mi ?’ (too much to count)

Click for Tuesday Challenging Route

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 here, 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 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 Visitor Center where we pick up the Ashuwillticook Rail Trail, rejoining the Regular Route.


Regular Route – Richmond – West Stockbridge – Alford – Great Barrington ~34 mi 2050’ (~27 mi with cut-off at the end)

Click for Wednesday Regular Route

Wednesday is move day! Only one route today so you can return with time to spare. We’ll be riding 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 – Stay Tuned

Likely to follow the Regular Route through these charming, “off the beaten track” towns.