4.3
(4)
34
riders
18
rides
Road cycling routes around Jaffrey are characterized by the scenic Monadnock Region, featuring a mix of rolling hills, dense forests, and serene lakes. The terrain includes varied elevations, with Mount Monadnock as a prominent landmark, though road cycling routes generally navigate its foothills and surrounding areas. The region offers a network of country roads and some rail trails, providing diverse surfaces for cyclists.
Last updated: May 16, 2026
5
riders
44.9km
02:09
410m
410m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
4
riders
65.3km
03:03
660m
660m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.

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4.0
(1)
4
riders
51.0km
02:15
470m
470m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
4
riders
37.4km
01:43
300m
300m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
4
riders
31.8km
01:29
410m
410m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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Popular around Jaffrey
Powder Mill Pond, spanning 419 acres, is an impoundment situated on the Contoocook River in Hillsborough County, southern New Hampshire, USA. The dam for the pond is positioned within the town of Bennington, with the water impounded reaching into the towns of Hancock and Greenfield. There is a gap in the trees at this point allowing you to see across the wetland towards the peaceful pond.
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This old covered bridge spans the Contoocook River and gives a lovely view of the river and Powdermill Pond Wildlife Management Area around the water. The area is particularly beautiful in Autumn when the trees leaves change to amber and crimson colors.
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This stretch of quiet country road, gives lovely views of the peaceful lake and surrounding woodland and grassland. Keep your eye out for the mixed bird species that inhabit the lake.
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This quiet lake and its beach are perfect for taking a rest off of the bike. With a lovely sandy beach to get into the water, the lake is perfect for a cool off on a summers day.
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The North Central Pathway is a paved multi-use pathway that stretches over 11 miles, following the Millers River.
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Wallace Pond is a scenic pond in Ashburnham, Massachusetts, just a few hundred yards from the border with New Hampshire. Rindge State Road crosses right over it, so as you ride, there is water on both sides of you. This is a great place to slow down and take in the views over the water and look for birds and other animals.
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Harrisville is a charming small town centered around a historic 19th-century industrial mill complex. The town is frequently photographed as an example of picturesque New England.
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There are 18 road cycling routes around Jaffrey, offering a variety of experiences. These include 2 easy routes and 16 moderate routes, catering to different skill levels.
Road cycling in the Monadnock Region, particularly around Jaffrey, is characterized by rolling hills, extensive forests, and picturesque lakes. While Mount Monadnock is a prominent landmark, routes generally navigate its foothills and surrounding areas, offering varied elevations and scenic country roads. You'll find a mix of paved surfaces and some rail trails.
Yes, Jaffrey offers routes suitable for families. For an easier ride, consider the North Central Pathway loop from Pearly Lake Wildlife Management Area, which is an easy 23.3-mile (37.4 km) route. The Monadnock Recreational Rail Trail also provides a generally flat, multi-use path that can be enjoyed by families.
Road cycling routes around Jaffrey offer beautiful views of the Monadnock Region's natural landscape, including lakes and forests. You might pass by areas with glimpses of Mount Monadnock itself. For specific landmarks, consider routes that offer views towards Mount Monadnock Summit or Thoreau's Seat. The region's lakes, such as Contoocook Lake and Thorndike Pond, also provide picturesque backdrops.
Yes, many road cycling routes in Jaffrey are designed as loops. For example, the popular Wallace Pond – North Central Pathway loop from Tetreault Park is a 27.9-mile (44.9 km) moderate route. Another option is the Powder Mill Pond – Forest Road covered bridge loop from Peterborough, which is 31.7 miles (51.0 km) long.
The Monadnock Region is beautiful throughout the warmer months. Spring offers lush greenery, while summer provides warm weather for longer rides. Autumn is particularly scenic with vibrant fall foliage, making it a popular time for cycling. Winter cycling is possible but conditions can be challenging due to snow and ice, especially on less-trafficked roads.
Yes, the region is dotted with beautiful lakes and ponds. The Lake beach loop from Fremont Conservation Land is a moderate 19.8-mile (31.8 km) route that takes you past a lake. Other routes may offer views of Contoocook Lake or Thorndike Pond, which are prominent water bodies in the area.
The road cycling routes in Jaffrey are highly rated by the komoot community, with an average score of 4.0 stars. Cyclists often praise the varied terrain, the scenic beauty of the Monadnock Region's forests and lakes, and the network of country roads that offer enjoyable rides.
While there are no routes explicitly rated as 'difficult' in the guide data, the Monadnock Region offers several moderate routes with significant elevation gain that can provide a good challenge. For instance, the Harrisville – Hardy Hill loop from Fremont Conservation Land is a moderate 40.9-mile (65.9 km) route with over 2,100 feet (660 meters) of elevation gain, offering a substantial ride for experienced cyclists.
Many routes start from locations with designated parking. For example, the Wallace Pond – North Central Pathway loop starts from Tetreault Park, and the Harrisville – Hardy Hill loop begins near Fremont Conservation Land. These are common starting points that typically offer parking facilities.
Yes, you can find routes that feature charming covered bridges. The Powder Mill Pond – Forest Road covered bridge loop from Peterborough is a 31.7-mile (51.0 km) route that leads through forested areas and past Powder Mill Pond, including a covered bridge as a scenic highlight.


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