5.0
(14)
215
riders
30
rides
Road cycling routes around Ashland traverse a landscape characterized by lake loops, river valleys, and rolling hills. The region features varied terrain, from gentler paths to more challenging ascents, with elevation gains present on many routes. Ashland is situated in the Rogue Valley at the base of the Siskiyou Mountains, offering diverse topography for road cyclists. The area provides a network of roads that connect natural features and local points of interest.
Last updated: July 2, 2026
5.0
(3)
43
riders
54.5km
02:27
580m
580m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
7
riders
41.1km
01:43
240m
240m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

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5
riders
63.6km
03:00
800m
800m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
7
riders
104km
04:47
1,150m
1,150m
Hard road ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride.
5
riders
36.4km
01:39
380m
380m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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Popular around Ashland
You'll love crossing this picturesque covered bridge with its wooden trusses in the heart of Ashland! Built in 1990, and right next to Little Squam Lake, it makes this place truly idyllic.
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From here, you'll have lovely views of this lake. This narrower part with trees on either side located at the northern end is exactly where its waters flow into Squam Lake, the second largest lake in New Hampshire.
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Sandwich Town Beach is a beautiful small beach set on the eastern shores of Sandwich Bay on Squam Lake. It is a truly beautiful spot but the beach is for Sandwich residents only.
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Squam Lake is a 6,791-acre body of water just south of the White Mountains. It served as the backdrop for the movie "On Golden Pond" and is a summertime destination in the Lakes Region of New Hampshire. The lake is dotted with 30 islands and is a prime nesting site for loons, bald eagles, and great blue herons.
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Livermore Falls State Forest encompasses scenic New England beauty, diverse ecosystems and scenic landscapes.
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A historic and very picturesque wooden bridge, traditional from the New England region. You can cross the bridge and you'll see the amazing wooden structure
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Scenic road with beautiful views of the mountains, fields, and folliage. Runs parallel to Mt Moosilauke Highway.
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Quiet road without much traffic that runs parallel to Mt Moosilauke Highway. Rolling hills with beautiful views of folliage & Baker River.
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There are over 30 road cycling routes around Ashland, offering a variety of options for different skill levels and preferences. These routes are highly rated by the komoot community, with an average score of 5.0 stars.
Yes, Ashland offers several easy road cycling routes suitable for beginners. For example, the Buffalo Road – Old Route 25 Scenic Road loop from Plymouth is an easy 25.6-mile (41.2 km) trail that takes you through scenic roads.
Road cycling routes in Ashland vary in length. You'll find options ranging from shorter rides, like the 18.4-mile (29.7 km) Squam River Covered Bridge – Shepard Hill loop from Pilote Forest, to longer excursions such as the 33.9-mile (54.5 km) Squam Lake loop from Ashland, and even longer routes like the 39.5-mile (63.5 km) Squam River Covered Bridge – Squam Lake loop from Holderness.
Yes, the region's diverse topography includes routes with significant elevation gains that provide challenging climbs. Routes like the Squam Lake loop from Ashland feature moderate elevation changes, while others can offer more demanding ascents for experienced cyclists.
Ashland's road cycling routes traverse a varied landscape characterized by lake loops, river valleys, and rolling hills. You'll encounter a mix of terrain, from gentler paths to more challenging ascents, with many routes featuring diverse elevation profiles.
Many routes in the Ashland area offer scenic views, particularly those that loop around Squam Lake or follow river valleys. The region's natural beauty provides numerous opportunities for picturesque stops and vistas.
The komoot community rates road cycling in Ashland highly, with an average score of 5.0 stars. Cyclists often praise the varied terrain, the beautiful lake circuits, and the network of roads that connect natural features and local points of interest.
Yes, many of Ashland's road cycling routes are designed as loops, allowing you to start and end at the same point. Examples include the popular Squam Lake loop from Ashland and the White Oak Pond – Squam River Covered Bridge loop from Plymouth.
Absolutely. The region is known for its charming covered bridges. The Squam River Covered Bridge – Shepard Hill loop from Pilote Forest is a great option that specifically includes a covered bridge along its path.
The best time for road biking in Ashland typically spans from spring through fall, when the weather is mild and the scenery is vibrant. Summer offers warm temperatures, while spring and fall provide cooler rides and beautiful foliage.
While popular routes can see more activity, the extensive network of roads around Ashland offers many opportunities to find quieter paths, especially on less-trafficked local roads or during off-peak hours. Exploring routes slightly further from central points can also lead to more serene rides.
For families or those seeking a more relaxed ride, Ashland offers easier routes with less elevation gain. The Buffalo Road – Old Route 25 Scenic Road loop from Plymouth is an easy option that could be suitable for families looking for a scenic and manageable ride.


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