4.0
(1)
27
riders
6
rides
Touring cycling routes around Ashland traverse diverse landscapes, from the foothills of the Siskiyou and Cascade mountain ranges to the scenic Rogue Valley. The region features varied terrain, including challenging climbs and descents through lush forests and open meadows. Cyclists can explore extensive trail networks that cater to different preferences, offering both paved multi-use paths and more demanding routes. This area provides a range of options for exploring its natural features by bike.
Last updated: May 21, 2026
4.0
(1)
15
riders
40.4km
02:33
470m
470m
Prepare for a challenging touring bicycle adventure on the Squam Lake loop, a difficult 25.1 miles (40.4 km) route that circles the picturesque lake. You will climb 1551 feet (473…
5
riders
28.6km
01:44
150m
150m
Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

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1
riders
23.6km
02:00
320m
320m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
3
riders
60.0km
04:53
800m
800m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
2
riders
73.1km
05:36
1,040m
1,040m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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Popular around Ashland
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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Do not bike on the main road, you look like you belong in Massachusetts doing this
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New Hampshire's covered bridge no. 41: a one-lane wooden bridge over the Pemi on a pretty back road.
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Mad River winds along Route 49. Great views & a great spot to hop off your bike & take a dip in the water.
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Touring cycling routes in Ashland offer a diverse range of terrain, from the challenging climbs and descents of the Siskiyou and Cascade mountain ranges to scenic rides through the Rogue Valley. You'll find routes traversing lush forests, open meadows, and extensive trail networks, including both paved multi-use paths and more demanding routes.
Yes, Ashland offers options for various skill levels. For an easier ride, consider the Baker Forest loop from Plymouth, which is 28.5 km (17.7 miles) and typically takes around 1 hour 43 minutes. The Bear Creek Greenway, though not listed as a specific komoot route here, is also a well-known paved multi-use trail ideal for easygoing rides with friends or family, connecting Ashland to nearby towns.
Ashland generally offers excellent cycling conditions for much of the year. Spring and fall provide pleasant temperatures and vibrant scenery. Summers are typically warm and dry, ideal for early morning or late afternoon rides. While winter can bring colder temperatures and some snow at higher elevations, lower-elevation paved trails like the Bear Creek Greenway may still be accessible.
Yes, many routes in the area are designed as loops, allowing you to start and end in the same location. An example is the Squam Lake loop — Holderness, a difficult 40.3 km (25 miles) route that offers varied scenery.
For experienced touring cyclists seeking a challenge, the Mad River from Lincoln Road loop from Common Man is a difficult 73.0 km (45.4 miles) route with significant elevation gain, typically taking over 5 hours. Another demanding option is the Sandwich Town Beach – Squam Lake loop from Ashland, a 62.0 km (38.5 miles) difficult path.
The diverse landscapes around Ashland, including forests and the Rogue Valley, are home to various wildlife. Cyclists might spot deer, various bird species, and smaller mammals. Always maintain a respectful distance and be aware of your surroundings, especially in more remote areas.
Absolutely. Many routes provide breathtaking views of the Rogue Valley and the distant Siskiyou and Cascade mountain peaks. The Ashland Watershed Loop, for instance, climbs to 5,000 feet, offering panoramic vistas before descending back to town. The Cascade-Siskiyou Scenic Bikeway also features diverse scenery and significant climbs with rewarding views.
The touring cycling routes in Ashland are highly rated by the komoot community, with an average score of 4.0 stars. Cyclists often praise the varied terrain, from challenging mountain foothills to scenic valley views, and the extensive network of paths that cater to different ability levels.
Yes, for a balanced challenge, consider the Campton Bog Pond loop from Common Man. This route is 23.6 km (14.7 miles) long, has a moderate difficulty rating, and typically takes around 2 hours to complete, offering a good mix of distance and elevation.
Yes, especially on routes that pass through or near towns. The Bear Creek Greenway, for example, offers convenient access to parks, restaurants, coffee shops, and bike shops as it connects Ashland to nearby communities like Talent, Phoenix, and Medford. Even on more rural routes, you'll often find small towns with amenities.
Beyond the routes themselves, Ashland is surrounded by natural beauty. You can explore the extensive trail system of the Ashland Watershed, enjoy the tranquil ponds and Ashland Creek in Lithia Park, or venture further to the ecologically significant Cascade-Siskiyou National Monument. Crater Lake National Park is also about two hours away for a breathtaking side trip.


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