This ride’s general location is Randolph. Scenery includes expansive views from the summit of Mount Cushman; the rest is a mix of wooded trails, farmlands, open meadows, and dirt roads lined with stone walls. This ride takes you to the top of Mount Cushman, which has an elevation of 2,750 feet. The ride uses the same Class 4 road built in the late 1800s. The gap goes through a saddle between Mount Cushman and Rochester Mountain. From the saddle the ride takes you on a ridge traverse of the Braintree Mts., past the footings of a former fire tower, to the summit and a clearing that faces west. The first half of the ride is on Class 3 dirt roads that climb gradually through rural farmland to the base of Randolph Gap. Then a steep out-and-back spur takes you to the top of Mount Cushman on a Class 4 double-track jeep road. Then you will descend through more scenic farmland. Just when your legs are about to give out, you climb a double-track jeep road that wanders between old stone walls through deep forests. The final descent brings you to paved VT 12 and an easy cruise back to the start for a total of 23.3 very challenging miles.


Activity Type Mountain Biking
Nearest Town Randolph
Length 23.3 total miles
Elevation Gain  2400 feet
Trail Type Loop
Skill Level Very difficult


Trailhead: The ride begins in the parking lot behind the New England Land Company. There is plenty of parking and a quick-stop convenience store across the street.

Latitude/Longitude: 43.927402,-72.666151

Directions: Exit the New England Land Company parking lot and turn right, heading for downtown Randolph. Cross a bridge and turn right onto School Street, just after the big white Bethany Congregational Church. The road is paved to the railroad tracks; after that it is dirt. Once you cross the railroad tracks, the road becomes School Street Extension.

Continue on this road, passing Bailey Tack and Howard’s Mill, climbing gradually and steadily. At 4.6 miles is a T-intersection; turn left onto Little Hollow Road. This is a nice, shady cruise between worn-down stone walls and picturesque house sites. Occasionally you have glimpses of the mountains ahead.

At 7.4 miles is a 4-way junction called Four Corners. On the far left corner is a stand of pines. Turn right and ride up an innocent-looking narrow road. Suddenly the road becomes very narrow and rocky. This is the base of Randolph Gap Road. You have a tough climb of more than 1 mile ahead of you.

The road is very rocky and steep at first, and you might have to walk a section or two, but this rough section is over soon and the road becomes very rideable, although still steep. A few waterbars give you a change to catch your breath. At 8.8 miles from the start you reach a 4-way trail intersection at the saddle between Rochester Mountain and Mount Cushman. Don’t get excited – you are not done climbing!

Turn right at the intersection and roll along the ridge on a double-track jeep trail. The trail may be muddy, but you can usually stay clear of the mud by riding around it. There is a steep, short pitch that takes you to the site of a former fire tower. Continue past the site and descend briefly. One more climb takes you to the summit of Mount Cushman, where the views to the west of the Green Mountains are stunning.

Retrace you steps to the 4-way junction and turn left to descend Randolph Gap Road back to Four Corners. Or, for an additional 1,000′ of climbing, go straight through the intersection and climb for 1.5 miles to the summit of Rochester Mountain, which has an elevation of 2,953′. This is a steep, rocky climb for experts only. You are rewarded again, but this time with endless views to the east of the White River Valley and the White Mountains in New Hampshire. Return to the 4-way junction for a total of 3 additional miles not included in this ride’s total mileage.

Once you have descended Randolph Gap Road and arrived at Four Corners, continue straight through this 4-way intersection on a rough jeep road, which becomes the Bethel-Gilead Road. At the Y-intersection with a white house on the left, bear right, crossing over a bridge. Continue descending this road until you see a key landmark on the right, an old tractor with a Buffalo Crossing sign attached to the front. Take the left road across from the tractor, immediately past the tan house. Climb steeply to a Y-intersection at 17.8 miles from the start. Bear left (not to the right up the driveway posted with a private drive sign). This left turn becomes and overgrown, Class 4, double-track jeep trail. The trail climbs gradually (you will ultimately gain 400′ since the turn at the tractor) and winds through the woods, often between parallel stone walls.

Stay on the mail trail at all times. Follow the occasional WRVTA signs that say Rand, pointing the way to Randolph. The jeep trail dumps you out onto a gravel road with a nice house to the right. Follow the road and just after the second house, turn right onto a trail under a power line. The trail does a hairpin right, so you are riding back toward the house. Stay on the main vein, a Class 4 road, which improves the further you descend. This is Spooner Road, which brings you to VT 12 at 21.3 miles. Turn left on pavement and ride for 2 miles, straight through downtown Randolph and back to the New England Land Company for a total of 23.3 difficult miles.



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