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Road cycling routes
United States
New Hampshire
Hillsborough County

Wilton

The best road cycling routes around Wilton

125

riders

54

rides

Road cycling around Wilton, New Hampshire, offers diverse terrain characterized by a patchwork landscape of hills, forests, and farmlands in the southern New Hampshire hill country. The region features challenging cycling loops with significant elevation gain, providing scenic views of the Monadnock area. Routes often traverse rural roads and historic villages, catering to cyclists seeking both demanding climbs and picturesque rides.

Best road cycling routes around Wilton

  • The most popular road cycling route is Milford to Pack Monadnock Mountain loop

Last updated: June 28, 2026

4

riders

#1.

Milford to Pack Monadnock Mountain loop

57.1km

02:55

930m

930m

Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.

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Hard

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate
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Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate

Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.

Moderate

4

riders

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate
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Tips from the Community

Threehats
May 26, 2024, Pack Monadnock Mountain

Wonderful panoramic views from the summit, well worth the hike up!

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Jamie S.
February 24, 2024, Wooding Pond

Wooding Pond is an attractive freshwater pond that is crossed by Shirley Hill Road in Goffstown, New Hampshire. This is a pretty spot to ride past as you are surrounded by water. It's also a great spot to look out for birds and other wildlife, as well as people fishing in the summer.

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Alex
February 15, 2024, Forest Road

This flat road runs along the lake on one side, with tall pines lining the other. It is a beautiful stretch to cycle on, with plenty of wildlife to see.

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Peak of South Uncanoonuc Mountain. There are many trails leading up to the peak, but there is also a paved road that takes you to the top. It is a challenging climb, but definitely worth it for the view!

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Pack Monadnock Mountain is the highest peak of the Wapack Mountain Range at 2,290 feet. From the top, there is a great view of the valleys around and the other nearby peaks. There is a road that leads to the peak, so there is parking, restrooms and water.

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The Stowell Road Covered Bridge is a newer covered bridge, as it was constructed in 1990. It spans the Baboosic Brook and is open to traffic. There is no parking next to the bridge, but you can pull off the road and go onto the grass nearby if you want to stop and get a closer look of the bridge.

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mtm05005
September 12, 2023, Tucker Brook Falls

Tucker Brook Falls is a great small waterfall tucked in the woods. It is not visible from the road, but if you walk your bike a couple of feet down a path, you will be able to get a view of the falls.

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Peak of South Uncanoonuc Mountain. There are many hiking trails leading up to the peak, but there is also a paved road that takes you to the top. It is a challenging climb, but definitely worth it for the view!

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Frequently Asked Questions

How many road cycling routes are available around Wilton, New Hampshire?

Komoot offers over 50 road cycling routes around Wilton, New Hampshire. These routes cater to various skill levels, from moderate rides to more advanced routes with substantial climbing, allowing cyclists to explore the region's diverse terrain.

Are there easy road cycling routes suitable for beginners in Wilton, New Hampshire?

Yes, Wilton, New Hampshire, offers several easier road cycling options. While many routes feature rolling hills, there are 8 routes classified as easy, providing a gentler introduction to the region's scenic landscapes. These routes are perfect for those looking for a less strenuous ride.

What kind of terrain can I expect on road cycling routes around Wilton, New Hampshire?

Road cycling around Wilton, New Hampshire, is characterized by a picturesque patchwork landscape of hills, forests, and farmlands. You'll encounter rolling hills and rural roads, with some routes featuring significant elevation gain, offering challenging climbs and scenic views of the Monadnock region.

Are there any long-distance road cycling routes in Wilton, New Hampshire?

Yes, the region is known for its longer, more challenging touring loops. For example, the Milford to Pack Monadnock Mountain loop is a difficult 35.5-mile route with significant elevation gain. Another option is the Wooding Pond – Stowell Road Covered Bridge loop from Lindabury Orchard, a moderate 33.4-mile ride.

Can I find circular road cycling routes around Wilton, New Hampshire?

Many of the road cycling routes around Wilton, New Hampshire, are designed as circular loops, allowing you to start and end at the same point. Examples include the Christian Hill – Forest Road loop from Lindabury Orchard and the Baboosic Lake loop from Lindabury Orchard, which offer varied terrain and scenic views.

What scenic viewpoints or attractions can I see along road cycling routes in Wilton, New Hampshire?

Road cycling routes in Wilton, New Hampshire, often provide scenic views of the Monadnock region and traverse historic villages. While riding, you might encounter natural attractions like Purgatory Falls or Tucker Brook Falls. The Wilton Riverwalk also offers a pleasant stroll along Stony Brook, where you might spot local wildlife.

Are there advanced road cycling routes for experienced cyclists near Wilton, New Hampshire?

Absolutely. Wilton, New Hampshire, offers challenging routes with significant elevation gain for advanced cyclists. The Milford to Pack Monadnock Mountain loop is classified as difficult, featuring over 3,000 feet of climbing over 35.5 miles. These routes provide demanding climbs and rewarding views.

What do other road cyclists enjoy most about road cycling in Wilton, New Hampshire?

Road cyclists frequently praise the diverse terrain, from rolling hills to challenging climbs, and the picturesque patchwork landscape of forests and farmlands. The opportunity to cycle through historic villages and enjoy scenic views of the Monadnock region is also a highlight for many.

Is it possible to find routes that pass through historic villages in Wilton, New Hampshire?

Yes, Wilton, New Hampshire, is known for its historic village tours. Many road cycling routes are designed to take you through charming, historic villages, allowing you to experience the rural routes and scenic landscapes while exploring the region's heritage.

Are there any specific routes that offer views of lakes or water bodies?

Yes, some routes provide views of local water bodies. The Baboosic Lake loop from Lindabury Orchard is a moderate 29.3-mile route that leads through varied terrain, including scenic views of Baboosic Lake.

What is the best time of year to go road cycling in Wilton, New Hampshire?

The region's 'patchwork landscape of hills, forests, and farmlands' makes it appealing for cycling throughout the warmer months. Spring, summer, and autumn generally offer pleasant conditions to enjoy the scenic views and diverse terrain, with autumn providing vibrant foliage.

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