5.0
(11)
482
riders
85
rides
Road cycling around Pepperell, Massachusetts, features a landscape characterized by the Nashua River and its associated rail trails, alongside quiet country roads. The region offers a mix of flat sections, particularly along the river, and gently rolling terrain with moderate elevation changes. This area provides varied routes suitable for different skill levels, from leisurely rides to longer excursions.
Last updated: July 2, 2026
5.0
(4)
165
riders
30.3km
01:31
100m
100m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
15
riders
54.9km
02:49
480m
480m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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2
riders
The Groton School Pond – Nashua River Rail Trail loop offers a pleasant road cycling experience, primarily featuring the smooth, flat terrain of the Nashua River Rail Trail. You'll pedal…
4
riders
87.5km
03:40
510m
510m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
6
riders
60.6km
02:43
460m
460m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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A quit river with some great views
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Classic New England covered bridge, restored and still in use. Small park on the east side, multiple good routes from the bridge west through Massachusetts and New Hampshire.
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Paved route through the woods, although best taken at a slow speed to both enjoy the scenery, and accommodate runners, joggers, walkers, and small kids just learning to ride. Save the road racing for out on the roads.
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0
The Nashua River Rail Trail is a paved trail that was constructed on an old railbed. It is completely traffic free, so it is a great place for a relaxed walk.
1
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There are only a handful of covered bridges in the state. This is the furthest east one
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One of the older trails in the state but a great one. Some lovely views of the river at various points
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There are over 80 road cycling routes in the Pepperell area, catering to various skill levels. This includes 31 easy routes, 51 moderate routes, and 5 more challenging options.
Yes, Pepperell offers several easy routes perfect for beginners and families. The Pepperell Covered Bridge – Nashua River Trailhead loop from Pepperell is an easy 10.7-mile path that provides scenic views. Another great option is the Nashua River Rail Trail – Nashua River Rail Trail loop from Shepley Hill, an 18.8-mile easy trail following the Nashua River.
For those seeking longer rides, the Mill Pond – Concord Monument Square loop from Shepley Hill is a moderate 54.4-mile (87.5 km) route. Another substantial option is the June's Wood – Quiet country road loop from June's Wood, which covers 34.1 miles (54.9 km) through quiet country roads.
Yes, many routes in Pepperell are designed as loops. Examples include the Nashua River Rail Trail – Nashua River Rail Trail loop from Shepley Hill and the Pepperell Covered Bridge – Nashua River Trailhead loop from Pepperell. These circular routes allow you to start and end at the same point.
Road cycling around Pepperell offers diverse scenery, including stretches along the scenic Nashua River, views of the historic Pepperell Covered Bridge, and peaceful rides through quiet country roads. You'll also encounter areas near June's Wood and various lakes like Groton School Pond.
Along the routes, you can see the historic Pepperell Covered Bridge and ride alongside the Nashua River Rail Trail. Other points of interest include Groton School Pond and the tranquil June's Wood.
The road cycling routes in Pepperell are highly rated by the komoot community, with an average score of 5.0 stars from over 10 reviews. Cyclists often praise the quiet country roads, the scenic Nashua River, and the variety of routes available for different skill levels.
Yes, the region is characterized by its rail trails. The Nashua River Rail Trail – Nashua River Rail Trail loop from Shepley Hill is a prime example, offering a pleasant ride along the scenic Nashua River.
The terrain around Pepperell features a mix of flat sections, particularly along the Nashua River, and gently rolling hills with moderate elevation changes. This provides a varied experience suitable for different preferences.
While road cycling is enjoyable in Pepperell for much of the year, spring and fall offer particularly pleasant conditions with mild temperatures and beautiful foliage. Summer is also popular, though it can be warmer.
Yes, some routes pass by local bodies of water. For instance, the Groton School Pond – Nashua River Rail Trail loop from Meredith Bissell Property offers views of Groton School Pond.


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