Hilltown Challenge Ride

Westfield, Massachusetts 01086

Hilltown Challenge Ride

Hilltown Challenge Ride Professional Review and Guide

"Just northwest of Springfield, delightful bicycling abounds in the small valley tucked between the East Mountain–Mount Tom range on the east and rugged, wooded hill country on the west. Lying in the small watershed of the Manhan River, the valley presents a harmonious blend of broad, gently rolling farms and stands of woodland, with views of the surrounding hills across the fields.

Start: Bickford’s Family Restraurant, Westfield. Length: 36.1 miles. Ride time: 2.5- 3 hours. Terrain: very hilly with two big climbs. The ride starts on the outskirts of Westfield, a small industrial city that for many years was best known as the home of Columbia bicycles. You’ll immediately head into farm country as you wind along the western edge of the valley on back roads to the handsome town of Southampton, with its magnificent old white church and a brick turn-of-the-twentieth-century library. From here you’ll head through prosperous farmland to Pequot Pond and return to Westfield, skirting the base of East Mountain."

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Trail Information

Nearby City
Trail Type
Skill Level
2.5 to 3 hours
Riding Time
200 feet
Trailhead Elevation
1,250 feet
Top Elevation
Greater Springfield Convention & Visitors Bureau
Local Contacts

Activity Feed

Jul 2018