The best road cycling routes around Pittsfield

There are 9 road cycling routes around Pittsfield featured in this guide, offering a range of distances and difficulties. These routes explore the scenic landscapes of the region, including lakes, rolling hills, and sections of the Taconic Mountain Range.

Road cycling around Pittsfield offers diverse terrain. You'll find paved rail trails like the Ashuwillticook Rail Trail, scenic roads passing by natural features such as Onota Lake and Pontoosuc Lake, and routes that traverse rolling hills and utilize low-volume roads. Some routes also feature significant elevation gain as they climb into the Taconic Mountain Range.

While the routes in this guide are rated moderate to difficult, the region offers excellent options for easier rides. The Ashuwillticook Rail Trail is a paved, car-free path perfect for families and beginners, offering beautiful Berkshire vistas. Pittsfield State Forest also features some paved bike paths suitable for less strenuous cycling.

Many routes offer stunning views of natural features. You can expect to see picturesque lakes like Onota Lake and Pontoosuc Lake. The Taconic Mountain Range provides a dramatic backdrop, and some routes offer vistas of Mount Greylock, the highest point in Massachusetts. Pittsfield State Forest, with its streams, waterfalls, and wild azalea fields, is another beautiful area to explore.

Yes, Pittsfield is a significant point along the multi-state Western New England Greenway (U.S. Bicycle Route 7). This route primarily uses low-volume, low-speed roads, offering a relaxing ride through Massachusetts and beyond. Some local routes, such as the Hayes Hill – Caverly Hill loop from Rochester Park and Ride, cover nearly 50 miles, providing a good long-distance option.

For family-friendly road cycling, the Ashuwillticook Rail Trail is an excellent choice. It's a paved, car-free trail that spans through several towns, offering a safe and enjoyable experience for all ages. While the routes in this guide are generally more challenging, the rail trail provides a great alternative for family outings.

Free parking is available at the Crane Avenue entrance in Pittsfield for the Ashuwillticook Rail Trail. For other routes, trailheads often have designated parking areas. It's advisable to check specific route details for parking information, but many routes start from locations with accessible parking.

Absolutely. The region around Pittsfield, particularly due to its proximity to the Taconic Mountain Range, offers routes with significant climbs. For example, the Halls Hill – Leavitt Hill loop from Gilmanton features over 960 meters of elevation gain, providing a demanding ride for experienced cyclists.

Yes, many of the road cycling routes in the Pittsfield area are designed as loops, allowing you to start and end at the same point. Examples include the Sanborn Hill – Jenness Hill loop from Alton Town Forest and the Hot Hole Pond – Shaw Field Conservation Area loop from Epsom Circle, which offer varied distances and scenery.

The spring, summer, and fall months generally offer the best conditions for road cycling in Pittsfield. Spring brings blooming wild azaleas in Pittsfield State Forest, while fall showcases vibrant foliage. Summers are pleasant, though it's always wise to check local weather forecasts. Some higher elevation areas, like the road to Berry Pond, are accessible by car from April to December, suggesting good cycling conditions during these months.

While Pittsfield State Forest is well-known for mountain biking, it also features paved bike paths. Some road cycling loops are available, such as the 'Gould Meadows loop from Stevens Corner'. The forest's 11,000 acres along the Taconic Mountain Range provide a beautiful backdrop for any ride. For more information on the forest, you can visit Housatonic Heritage.

Yes, some scenic road routes in the Pittsfield region extend into New York State, offering diverse terrain and views. Additionally, Pittsfield is part of the Western New England Greenway (U.S. Bicycle Route 7), which is a multi-state route connecting Connecticut, Massachusetts, and Vermont.