Bruce Freeman Rail Trail
The Bruce Freeman Rail Trail runs just over 20 miles from Sudbury to Lowell. In-between, the trail passes through Concord, Acton, Carlisle, Westford and Chelmsford. At the Sudbury end, close to Route 20, it connects to the Mass Central Rail Trail. There is a planned extension from Sudbury into Framingham.
The trail is well maintained with lights at road crossings. It is a well-used trail at peak times. There are parking areas at each terminus and in each of the communities along the trail. There is parking adjacent to Teamworks in Acton close to the midpoint.
This is a great trail for long rides. Some of the highlights include: the Sudbury River crossings, wetlands and ponds, countryside, stone walls, Concord Junction, the Route 2 Overpass, swimming ponds, woodland corridors, Graniteville and Forge villages, stone quarries, Chelmsford Village and Freeman Lake.
Assabet River Rail Trail
The Assabet River Rail Trail runs 5.8 miles from Marlborough into Hudson. (There is a disconnected northern portion of the trail as well). In Hudson it connects to the Mass Central Rail Trail. Trail use is consistent, but not overwhelming. In Hudson, there is parking at the intersection with the Mass Central trail. In Marlborough there is parking very close to the terminus across from Kelleher field.
This trail has more hills than the other trails on the list, but that only makes it more interesting. The Hudson portion passes the downtown area with restaurants and at least two brewpubs, also interesting!
Mass Central Rail Trail
The Mass Central Rail Trail connects the Bruce Freeman Rail Trail in Sudbury to the Assabet River Rail Trail in Hudson. It runs a distance of 7.6 miles. (There is an unconnected section in Wayland and Waltham). It's a beautiful new trail through the woods, passing a golf course and across a wetlands area. The trail is gaining in usage, but it's typically the least crowded of any trails on this list.
The parking area at the intersection of the Bruce Freeman trail and the Mass Central trail in Sudbury is insufficient for the demand. The parking at the Mass Central trail / Assabet River trail in Hudson is better.
It's a pleasant ride starting at the Sudbury end, riding to the Hudson end, connecting to the Assabet River trail and riding into downtown Hudson for a snack. There are a couple of brewpubs in the area as well.
Upper Charles Rail Trail
The Upper Charles Rail Trail runs 13.9 from Milford/Hopkinton to Sherborn/Holliston. The 7.2 mile Milford section is paved. The 6.7 mile Holliston section is hard-packed stone dust suitable for all bikes. The 27.8 mile round trip makes for a great day.
There is parking at the Milford terminus on Route 85. There are only a few spots at the Sherborn end point, but there are more on Mayflower Landing in Holliston.
In Holliston, the trail passes over the Bogastow Brook Viaduct and through the Phipps Tunnel. It passes through the downtown area along Route 135, which provides places to take a break or eat lunch.
In Milford, the trail passes Louisa Lake Park, Milford Pond, close to the granite quarry area, under Route 495, crosses East Main Street, and swings around Fino Field. Lots of places to takes breaks. Lots of restaurants.
Cochichuate Rail Trail
The Cochichuate Rail Trail runs 3.7 miles from School Street in Saxonville, Framingham to the Natick Center.
Nashua River Rail Trail
The Nashua River Rail Trail runs for 12.5-miles from downtown Ayer, Massachusetts, north through Groton, Pepperell, and Dunstable, to Nashua, New Hampshire. There is parking at the Ayer MBTA commuter rail on the southern end and at the Gilson Road terminus on the northern end, as well at several locations in-between. The 25-mile out-and-back distance is perfect for a weekend ride.
The trail isn't as smooth as some of the newer trails on the list, but it's still in great condition. We're just spoiled! Downtown Ayer is home to the MBTA Commuter Rail station, local diners, cafes, and shops. The trail passes Groton School Pond and J. Harry Rich State Forest. The Groton Center Spur is a bridge over Main Street leading to Groton Center. The trail proceeds past Pepperell Pond, more wetlands and Pepperell Town Center, with its ice cream shop and restaurant. Then, the MA/NH Border and forest corridors.
Minuteman Rail Trail
The Minuteman Rail Trail is a popular 10-mile trail leading from Bedford to Cambridge, through Lexington and Arlington. The 20-mile round trip distance, and the attractions along the way make it an attractive ride. There is parking at each end, at Bedford Depot and at Alewife MBTA Red Line station.
From Alewife there is a connection to the Cambridge Linear Park and Somerville Community Path, which carries riders into Davis Square, Somerville and beyond. The Somerville Community Path Extension continues on the other side of Davis Square and runs alongside the Green Line all the way to Lechemere, where one can connect to the Charles River Bike Path network. (Note: there is construction on portions of the Cambridge and Somerville trails in Fall 2026).
From Bedford Depot, there are connections to the Bedford Narrow Gauge Rail Trail (3 miles unpaved) and the Reformatory Branch Trail (4 miles dirt/gravel trail).
The Minuteman trail gets crowded at peak times. There are many historical and culinary attractions around Lexington Center, Arlington Center, Alewife and Davis Square. Recreation opportunities include Parker Meadow, Great Meadows, Spy Pond Park, Arlington Reservoir & Beach and Alewife Brook Reservation.
