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Routes
Road cycling routes
United States
Vermont
Windham County

Whitingham

The best road cycling routes around Whitingham

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Road cycling around Whitingham, Vermont, features a landscape of rolling hills, dense forests, and clear lakes. The region offers varied terrain with significant elevation changes, catering to different fitness levels. Cyclists can find routes with well-paved surfaces and scenic views of natural features like the Harriman Reservoir and the Deerfield River. Elevations range from 1,500 to over 2,000 feet, contributing to diverse cycling experiences.

Best road cycling routes around Whitingham

  • The most popular road cycling route is View of the Deerfield River – Hoosac Tunnel East Portal loop from Whitingham, a 31.6 miles (50.8 km) trail that takes 2 hours 28 minutes to complete. This moderate route offers views of the Deerfield River.
  • Another top favourite among local road cyclists is Hoosac Tunnel East Portal – Jarvis Hill loop from Whitingham, a difficult 42.9 miles (69.0 km) path. This route includes substantial elevation gain through the region's hilly terrain.
  • Local road cyclists also love the Waterfall – Porter Hill loop from Whitingham, a 20.5 miles (33.0 km) trail leading through forested areas and past hills, often completed in about 1 hour 47 minutes.
  • Road cycling around Whitingham is defined by rolling hills, forests, and views of lakes and rivers. The network offers options for different ability levels, from moderate climbs to more strenuous ascents.
  • The guide includes highly-rated routes that showcase the best of the region's landscape. More than 10 road cyclists have used komoot to explore Whitingham's varied terrain.

Last updated: May 16, 2026

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#1.

View of the Deerfield River – Hoosac Tunnel East Portal loop from Whitingham

50.8km

02:28

700m

700m

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

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Moderate

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

Hard
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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

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

Moderate

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Tips from the Community

Tyler Sanders
February 27, 2024, Pelham Lake Beach

Named after Fort Pelham from the French and Indian War, the lake provides a pleasant view as you ride, along with a beach area for cooling off if you decide to take a break. Additionally, there are miles of trails surrounding the lake to explore if you choose to combine your ride with some hiking.

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This 40 acre woodland was donated to the Franklin Land Trust by Alastair Maitland in 1992. This cool stretch of road takes you along the forest offering shaded roads in the summer time and amazing foliage colors in the fall. The forest is popular with bird-watchers, so keep your eyes peeled as you ride through here, you never know what you might see.

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Historic covered bridges such as this one are traditional in the area, and it is great to see them maintained. The Bissel Covered Bridge was built in 1881. By the mid-20th century the bridge was due to be replaced by a modern steel and concrete structure. The local town opposed the new structure, and the original bridge was rebuilt and kept to the original specifications. The bridge still features a wooden structure and wooden floor.

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Mill Brook Reservoir is a small lake surrounded by trees. If you pull off the main road by the old covered bridge there is a viewing platform where you can see the waterfall from Mill Brook as it fills the reservoir.

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The Hoosac Tunnel is a working 4.75-mile (7.64 km) active freight railroad tunnel in western Massachusetts. The East Portal of the tunnel can be found in the town of Florida. It is on the big bend of the Deerfield River and not far from the roadside, so it is easy to go and visit.

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Here you can have a wonderful view of the Deerfield River. This 122-kilometer-long river has its source in the Green Mountains, south of Vermont. It is the right tributary of the Connecticut River, which flows through the US states of Vermont and Massachusetts.

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Frequently Asked Questions

What kind of terrain can I expect on road cycling routes in Whitingham?

Whitingham offers a diverse road cycling experience characterized by rolling hills, dense forests, and clear lakes. You'll find routes with significant elevation changes, ranging from moderate climbs to more strenuous ascents that can exceed 3,000 feet. Vermont is known for its hilly terrain, with grades potentially exceeding 10 percent on extended climbs, providing options for various fitness levels.

What scenic views and natural features will I encounter on road cycling routes in Whitingham?

Road cycling routes in Whitingham often feature picturesque views of the region's natural beauty. You can expect to see the expansive Harriman Reservoir (Lake Whitingham) with the Green Mountains in the background, sections along the Deerfield River, and lush forested areas. Some routes may also offer glimpses of the Green Mountain National Forest and the scenic Route 100 Scenic Byway, praised for its breathtaking views.

How long are the road cycling routes around Whitingham?

The road cycling routes around Whitingham vary in length. For example, the View of the Deerfield River – Hoosac Tunnel East Portal loop from Whitingham is about 31.6 miles (50.8 km), while the Hoosac Tunnel East Portal – Jarvis Hill loop from Whitingham extends to 42.9 miles (69.0 km). You'll find options ranging from approximately 27 miles (44 km) to over 42 miles (69 km), catering to different preferences for ride duration.

When is the best time of year for road cycling in Whitingham?

The best time for road cycling in Whitingham is generally from spring through fall. The region is particularly stunning during the fall foliage season, which is even celebrated with the annual 'Hungry Lion Bicycle Tour'. While some routes may have unpaved segments, the main roads are typically well-maintained for cycling during these seasons. Winter cycling is possible but requires specific gear and awareness of conditions.

Are there family-friendly road cycling routes in Whitingham?

While Whitingham's road cycling routes are known for their varied terrain and significant elevation changes, which can be challenging, there are options that might be suitable for families with older children or those comfortable with moderate climbs. The region's quiet back roads offer a peaceful environment away from heavy traffic. Always check the route's elevation profile and distance to ensure it matches your family's ability.

Are road cycling routes in Whitingham suitable for cycling with dogs?

Road cycling routes in Whitingham are primarily on public roads and are generally not specifically designed for cycling with dogs. While some areas might allow dogs on leash, it's important to consider the safety of your pet on roads with traffic and varying surfaces. For off-road activities with dogs, nearby natural areas like the Green Mountain National Forest might offer more suitable options for hiking or walking.

Are there any loop road cycling routes in Whitingham?

Yes, many of the road cycling routes around Whitingham are designed as loops, allowing you to start and end at the same point. Examples include the View of the Deerfield River – Hoosac Tunnel East Portal loop from Whitingham, the Hoosac Tunnel East Portal – Jarvis Hill loop from Whitingham, and the Mirror Lake – Snow Lake loop from Wilmington. These loops offer convenient ways to explore the region's landscapes.

What is the difficulty level of road cycling routes in Whitingham?

The road cycling routes in Whitingham cater to a range of abilities. You'll find several moderate routes, such as the View of the Deerfield River – Hoosac Tunnel East Portal loop from Whitingham, which offers a good challenge without being overly strenuous. There are also more difficult options, like the Hoosac Tunnel East Portal – Jarvis Hill loop from Whitingham, which includes substantial elevation gain and requires good to very good fitness.

Are there cafes or places to stop along the road cycling routes in Whitingham?

Whitingham and the surrounding towns offer a tranquil, rural cycling experience. While specific cafes directly on every route might be limited, the region's reputation for hospitable accommodations and local establishments means you can find places to refuel in nearby villages. Planning your route to pass through towns like Wilmington can provide opportunities for stops.

What are the road conditions like for cycling in Whitingham?

Many road cycling routes in Whitingham feature well-paved surfaces, ensuring a smooth ride. However, it's worth noting that some segments, especially on quieter back roads, may be unpaved. This mix can appeal to cyclists looking for diverse surfaces. Vermont is known for its scenic, quiet back roads, which generally offer pleasant cycling conditions.

How many road cycling routes are available around Whitingham?

There are several road cycling routes available around Whitingham, with komoot featuring at least five highly-rated options. These routes showcase the best of the region's landscape and cater to various ability levels, from moderate climbs to more strenuous ascents.

What makes Whitingham a good destination for road cycling?

Whitingham is an excellent destination for road cycling due to its blend of picturesque landscapes, diverse and often challenging terrain, and tranquil natural environment. Cyclists can enjoy stunning views of lakes, rivers, and forests, experience significant elevation changes, and ride on quiet back roads. The area's appreciation for cycling is also highlighted by events like the annual 'Hungry Lion Bicycle Tour'.

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