Where To Ride in the Berkshires
Come and bicycle Great Barrington
When it comes to road cycling, Great Barrington and the surrounding area are some what of a hidden gem (SHHH don't tell anyone). If I was to tell anyone where they should ride their bike around Southern Berkshire county, I would direct them to this website page! Check out the links below for some great on road cycling routes.
If you are looking to go on on a bicycle ride on a rail trail, or you don't want to ride on the road with cars. Here are a few local routes for you...
Recomended Road Routes
20 Mile Alford Loop
Classic 20 mile route from the Great Barrington shop takes you through Alford, beautiful vistas and quiet roads makes this a favorite ride.
30 mile - Ride to Southfield Store and back
The Southfield Store is a destination not to be missed, great coffee, tasty baked goods and awesome lunch options. Paired with some beautiful quiet roads, this is one of our favorite summer rides!
25 mile - GB Shop to Ashley Falls and Back
Relaxing 25 Mile route South to Ashley Falls, over to S. Egremont, and back. Mostly on back roads, some short sections on Rt. 7.
28 mile - Ride to Hillsdale and back
Wow, great ride to NY state and back.
17 mile - Egremont loop
Go do the Egremont loop!
29 mile - Tyringham loop
Go check out the infamous WALL OF PAIN
30 mile - Lenox mountain loop
Riding north from the Great Barrington shop, up rte 183 to Lenox Mountain. Up and over into Richmond, winding into West Stockbridge and down East road in Alford.
24 mile - Lake Buel loop
Ride out from the GB shop towards Ski Butternut, turn right down Lake Buel Rd. As you roll through New Marlboro, be sure to stop at mile marker 10.3 to check out Umpachene Falls and cool off in the water. Once you get into Sheffield the hills mellow out and the rest of the ride is pretty mellow as you navigate up Boardman St.
Come and cycle Pittsfield
Pittsfield is home to some of the best on road AND off road cycling in the Berkshires.
If you are looking to go on on a bicycle ride on a rail trail, or you don't want to ride on the road with cars. Here are a few local routes for you...
Recomended Road Routes
33 mile - Lee and Washington loop
Ride to Lee and come back through Washington
25 mile - Pittsfield loop
Clockwise loop leaving from the Pittsfield Berkshire Bike and Board location. Passes by Onota Lake, Pontoosuc Lake, and Cheshire Reservoir. Rides on the Ashuwillticook rail trail for a few miles.
Pittsfield State Forest MTB Routes
Wether you are a seasoned pro on the MTB or a brand new rider, you will find something fun to ride in Pittsfield State Forest! Not familiar with riding at PSF? Here are some recommended routes to get you started! All of these recommended rides are linked to the TrailForks app and website, an amazing resource for finding and then navigating MTB trails. Download the app and load the maps before you leave to ride, don't worry you don't need cell service once you load the maps. These routes all leave from the Lulu Brook Parking lot and enter the woods just to the right of the wooden cabin by the paved road.
Honey Bear Loop - 1.3 miles (Beginner)
Super fun and mellow trail, one recommendation would be to ride this trail clockwise. The Trailforks loop shows to ride this trail counter clockwise.
Snoopy Loop - 8 Miles (Intermediate)
Loved the Honey Bear Loop but want more? This tour of the PSF family trails will get you on most of the trails in the network. It is said that you can see an outline of Snoopy in the map.... I will leave that to your imagination.
Up Honolulu and down Turner - 7 miles (Advanced)
Hope you brought your climbing legs for this classic Pittsfield State Forest loop. Climb up the switchbacks of Honolulu trail, navigate the top of the mountain on Tapanzee trail. Once you hit the paved road check out the amazing view of NY state just past the turn for Turner trailhead drop in. The ride down Turner trail will be a great reward for all the climbing you just did, maybe you will come back for another lap... I would recommend descending down Parker Brook
Come and cycle Hudson
Wether you are looking for some on road cycling, some rail trail cruzing, or a nice singletrack ride in the woods. Hudson has some great offerings, Check out our recommended routes below.
If you are looking to go on on a bicycle ride on a rail trail, or you don't want to ride on the road with cars. Here are a few local routes for you...
Recomended Road Routes
17 mile - Hudson South route
Leaving from our Hudson location going south.
21 mile - Hudson North loop
Leaving from our Hudson location going north.
Recomended Mountain Bike Trails
Greenport Conservation Area MTB trails
7 minute drive and 10 minute ride from our Hudson location. Mountain biking for all levels.
Local rail trails & car free bike rides!
Ashuwillticook Rail Trail
13 mile rail trail runs from Pittsfield to Adams with amazing Berkshire vistas.
Harlem Valley Rail Trail
26 miles of paved rail trail, the southern most part starts in Wassaic NY and runs north to Copake NY.
Empire State Trail Hudson
26 miles of paved rail trail, the southern most part starts in Wassaic NY and runs north to Copake NY.