Biking in Vermont is a fantastic way to see the picturesque rolling green farmland
and the renowned seasonal foliage.  There are many loops to explore not
to mention numerous out-and-back rides through this gorgeous area.  People
flock to the area, especially during the leaf-peeping season, to ride the
solemn country roads. This section offers rides on paved roads with varying
degrees of physical demands.

Middlebury-Addison Loop: 38 miles	Middlebury Gap: 42 miles
Middlebury-Cornwall-Shoreham Loop: 30 miles	Middlebury-Appalachian Gap: 73 miles of pain
Cider Mill Loop: 9.5 miles

Middlebury-Bridport-Chimney Point-Addison
Loop
Length: 38 miles

Begin riding west out Route 125 (toward the blinking light) for 8 miles to
Bridport and onto Chimney Point (there is a short section where Route 125
is the same as Route 22A). Turn north (right) onto Route17 and continue 8
miles east to Addison. Four miles past Addison, turn south (right) onto Route
23 following this road back to campus.

Middlebury-Cornwall-Shoreham Loop
Length: 30 miles

Start the ride following Route 30 from campus for four miles to Cornwall. Turn
right on Route 74 and ride 12 miles to Shoreham. Head south briefly on Route
22A before turning east (left) onto Richville Road. Ride through Shoreham
Center to the junction with Route 30 in Whiting. Turn north (left) and return
to campus.

Cider Mill Loop
Length: 9.5 miles

From campus, ride out Route 30 past the athletic center and the golf course.
About one mile past the golf course, turn north (right) on Cider Mill Road.
Follow this road as it passes orchards and overlooks the college to the blinking
light on Route 125. Cross 125, staying on Cider Mill Road and meet up with
Route 23 (Weybridge St.) Turn right and pedal back to campus.

Gap Rides

These rides are significantly more demanding than the previous rides. There
are four ridable gaps over the spine of the Green Mountains: Middlebury, Lincoln,
Appalachian and Brandon. Some would consider the ride over the mountains a
healthy dose of exercise. Others will find these rides ludicrous-don’t
feel ashamed.

Middlebury Gap: Middlebury to Hancock
Length: 42 miles

The first part of the rides takes you from Middlebury to East Middlebury south
along Route 7 out of campus and then east (left) onto Route 125. From here
the road is steep and windy to Ripton followed by easier riding past Breadloaf
and the Robert Frost Trail. A final difficult climb reaches the top of the
Middlebury Gap signified by the Long Trail, not far past the Snow Bowl. This
may be a good time to turn around if you’re not feeling you could climb
up the mountain again because once you bomb down to Hancock, the only way
back is over the mountain again.

Variation: If you say to yourself “I’ve seen that gap, what’s
next?” head south on Route 100 in Hancock, through Rochester
to Route 73. Turn back toward the mountains (right) and head over
the Brandon Gap and meet back up with Route 7 in Brandon.

Middlebury-Appalachian Gap:
Middlebury, Bristol-Waitsfield-Hancock
Length: 73 miles of pain

From Middlebury, ride to Bristol by way of Route 116. Follow 116 north through
Bristol to Route 17, which takes you over the App gap to Waitsfield. Turn
south (right) on Route 100 to Hancock. In Hancock, turn west (right) on Route
125 to return via the Middlebury Gap

Additional Resources

25 Bicycle Tours in Vermont, John Friedin 1996