Daily Itinerary
Arrival Day
You may arrive in Windsor at the time of your choosing, as there are no activities planned for your arrival day. Of course, the earlier you arrive, the more time you have to take advantage of the sights and charms of this historic town on the Connecticut River.
Known as the birthplace of the “free and independent State of Vermont” Windsor’s Historic District includes its “Old Constitution House,” the American Precision Museum (birthplace of the interchangeable parts concept for the machine tool trades) and numerous historically noted homes and markers.
Stage 1
For the first half of the day’s ride you’ll cycle in the shadow of Mount Ascutney, the highest peak in the area, unmistakable as it rises considerably higher than any of the surrounding peaks. After about 7 miles, and with most of your climbing behind you, you arrive in the tiny hamlet of Brownsville. From here you’ll enjoy gorgeous, easy cycling along unpaved roads winding along forested river shores. You’ll also encounter your second covered bridge.
In Perkinsville you’ll begin following the course of the Black River — rarely out of view for the remainder of your ride — and you’ll get a glimpse of yet another covered bridge. You’ll enjoy easy riverside cycling with only an occasional rise and fall in the roadway as you make your way to Cavendish and Proctorsville. As you pass through these twin villages the peak of Okemo Mountain looms larger and larger, beckoning you on to Ludlow, which sits at the base of the mountain. At 3,344 feet, Okemo is the tallest peak in this part of Vermont. Rising almost 2200 feet from the valley floor, Okemo features the largest vertical drop all of Vermont ski resorts.
Though you may choose to stay in the Village to take advantage of its shopping and dining options, you may also choose “a relaxing escape for urban and world weariness” Ludlow’s Echo Lake Inn has been characterized by Vermont Magazine. The Inn offers a large swimming pool, lake access (canoeing and swimming), as well as an award winning restaurant.
Stage 2
This day’s gorgeous ride takes you into the Green Mountains. Though you won’t be climbing any mountains, from Ludlow, you’ll slowly climb to a breathtaking ridge where you’ll enjoy the splendid wooded scenery and sweeping vistas of the Green Mountain National Forest. Because of this challenging climb we’ve kept the day’s mileage fairly short so that you can relax and savor the experience. Your ride tops out at the tiny hamlet of Belmont, with its classic church, general store, and post office, before descending to your next destination, Weston.
With one foot firmly planted in the foothills of the Green Mountain National Forest and the other in the fertile West River valley, Weston has come to exemplify the Vermont travel experience. Anchored by one of the most picturesque village greens in Vermont, the entire village is listed on the National Register of Historic Places. With hills rising prominently on all sides and a crystal clear brook running through the center of town, Weston is a veritable looking glass back to the early 19th century. Historic homes and antique shops, museum, galleries, gardens, inns, artists, and shops of all shapes and sizes grace the village’s main street. Other attractions include the original Vermont Country Store, source of Vermont products; the renowned Weston Playhouse, Vermont’s oldest professional theatre company: and the famous Weston Priory, a Benedictine monastery and one of the last of its kind.
Stage 3
From Weston, you’ll enjoy beautiful sweeping vistas as you descend into the fun little village of Londonderry. From Londonderry, you’ll head east along an ancient roadway named Popple Dungeon (so named for its dense canopy) to one of three lovely villages, depending upon availability.
In Perkinsville, you’ll stay at the much sought-after Inn at Weathersfield known for its fine dining and culinary classes (a two night minimum is often required); in Grafton, you’ll stay at the Inn at Grafton known as one of New England’s premier “destination wedding venues” in the heart of southern Vermont’s most scenic, tranquil village; in Chester, you’ll stay at the finely-appointed and stately Inn Victoria or the rustic, Fullerton Inn with its lodge-like atmosphere each located on Chester’s historic and lively village green.
No matter which route is taken on this day, you’ll cycle along a route of gently rolling green hills offering splendid views of family-owned valley farmsteads, forested ridges, and gurgling brooks often on historic roadways lined with centuries old stone walls.
Stage 4
On your final day of cycling, you’ll return to the mighty Connecticut River Valley. The valley boasts the richest agricultural soils in New England. Maple syrup, apples, corn, berries, and pumpkins are grown / produced in abundance throughout the valley. About halfway through the required portion of your ride, you’ll pass over the mighty Connecticut River which forms the border between Vermont and New Hampshire and continue north through lovely rural New Hampshire where you’ll have plenty of opportunities to sample the ample bounty of the region.
Upon reaching the Windsor-Cornish Covered Bridge, which is the world’s longest dual span covered bridge, we highly recommend continuing your journey north along picturesque River Road with a stop at the magnificent former home, lush gardens, and art-filled studios of sculptor Augustus Saint-Gaudens in Cornish.
