“Before ordering your tour, jot down the towns you’ll be staying in then, go to the Accommodations page and jot down which inns you like most in those towns. Doing so will make completing your order fast and easy.”
Brattleboro is a lively southern Vermont arts and cultural center, ideal for window shopping, gallery hopping, people watching, participating in a walking tour, canoeing on the Connecticut River, hiking the trails of the Brattleboro Retreat or visiting the Retreat’s Petting Farm, buying Vermont handcrafts, relaxing over a locally brewed beer, catching a movie or some live music, and of course, enjoying any one of a variety of exciting eateries and fine restaurants.
Following breakfast on your first full day in Brattleboro, you will attend a brief orientation at your hotel or B&B, test ride your bicycle, and then begin the first of your day-trip rides, or spokes.
Brattleboro Spokes: We offer 7 day trip rides from our Brattleboro hub. Each ride features stunning scenery along roads that are generally free of heavy vehicular traffic. The rides vary in length and degree of difficulty. You are free to do as many or as few rides as you wish.
This beautiful ride follows the course of the West River from its mouth in Brattleboro to the quintessentially Vermont village of Newfane, one of New England’s most beautiful villages. The terrain of this ride is easy overall, with just some minor exceptions. On this ride you will have the opportunity to:
Dummerston and Williamsville are tiny picturesque 18th century villages that continue to thrive. This challenging ride takes you first to Dummerston Center, set atop the ridge that rises between the Connecticut River and the West River Valleys. As the route continues you’ll enjoy a thrilling extremely steep descent to the West Dummerston Covered Bridge and swimming area.
Following easy cycling along the West River you climb the next ridge to reach the beautiful hollow in which Williamsville sits with its covered bridge spanning the Rock River.
The most challenging of the Brattleboro spokes, this ride follows the mighty Connecticut River, which forms the border between Vermont and New Hampshire. Though cycling in the fertile, orchard-studded valley carved by the river, the terrain is gently rolling, with occasional rises providing beautiful views of the mountains just across the river. You arrive shortly in the quintessentially Vermont village of Putney. Known as a local Mecca for arts and crafts, you’ll have the opportunity to visit the many artisan’s shops that are established here.
Following your Putney visit the route climbs up tranquil forested slopes for a thrilling ride along rivers rushing through the woods. After passing through pretty Dummerston Center your route plunges back down to Brattleboro by way of Naulakha, Rudyard Kipling’s treasured home in Vermont.
Cross the bridge from Brattleboro and you have arrived in New Hampshire. This moderately challenging ride follows the course of the Connecticut River on the New Hampshire side along a quiet road that rolls along the forested shoreline with splendid river views.
The route then turns inland to sleepy villages and one of the ride’s highlights: stunning Lake Spofford, a crystal clear sea of deep blue surrounded by thickly forested hills. You’ll want to bring your swimsuit for a dip at the sandy public beach. The return ride to Brattleboro features thrilling descents and gorgeous views of the Vermont mountains.
This very bucolic ride with easy-to-moderate cycling takes you west to Brattleboro’s Creamery Covered Bridge, before turning south for some wonderful cycling in the hollows between the mountain ridges south of Brattleboro. The route takes you briefly into Massachusetts by way of a shaded, unpaved road that parallels a beautiful cascading river; and then brings you back into Vermont through beautifully rolling areas mixed with forests and dairy farms. Back in Brattleboro, you will pass the uniquely designed buildings that comprise the former Estey Organ factory.
Experience three New England states over the course of this fascinating 33-mile loop! On this moderately challenging ride you will see the discernable differences between these neighboring states — in their architecture, land use, and geography. Beginning in downtown Brattleboro, you immediately cross the mighty Connecticut River into New Hampshire, where you follow the course of the river to Hinsdale, NH. There you head south through the forest to historic Northfield, Massachusetts. Then, after a stretch of dazzling green beauty, you turn north again and re-enter Vermont, hugging the left bank of the Connecticut River, with gorgeous views of the surrounding mountains and riverside. A truly remarkable ride!
Your route to Bellows Falls follows the mighty Connecticut River northward, which forms the border between Vermont and New Hampshire. Though cycling in the fertile, orchard-studded valley carved by the river, the terrain is gently rolling, with occasional rises providing beautiful views of the mountains just across the river. You arrive shortly in the quintessentially Vermont village of Putney, known as a Mecca for arts and crafts, and a wonderful opportunity to break and refuel.
Beyond Putney, your route takes you down to the riverside on a quiet dirt road before reaching Westminster. In Westminster, you cross the river to the New Hampshire side and the beautiful village of Walpole, another great opportunity to take a break and enjoy a tasty treat at locally renowned Burdick’s Chocolates. Just ahead, the mountains begin to close in on you, creating Bellows Falls’ dramatic setting. Crossing back into Vermont, you reach the day’s final destination, Bellows Falls.
Bellows Falls Hub: Bellows Falls was a manufacturing powerhouse in the 19th century, putting to use the massive energy of the falls for which it is named. The old factories are mostly gone now, but the vestiges of that prosperous era remain in the Victorian mansions that comprise the town’s registered historic district. (You can even overnight in one, if you wish.) Bellows Falls is a wonderful place for strolling and soaking in the New England atmosphere.
Bellows Falls Spokes: We offer 4 day-trip rides from our Bellows Falls hub. Each ride features stunning scenery along roads that are generally quiet. The rides vary in length and degree of difficulty. You are free to do as many or as few rides as you wish.
This beautiful ride follows the course of the Saxtons River, from Bellows Falls to Grafton, one of New England’s most beautiful villages. When you reach Grafton, don’t be surprised if you just want to sit for hours drinking in the beauty of its 19th century buildings and lovely setting between the surrounding mountain ridges. If you can motivate yourself into action, however, you may take advantage of the many art galleries, the local museum, Grafton’s covered bridge, and the original Grafton Village Cheese Company, where a tremendous variety of cheeses are produced and sold. There is also the Grafton Ponds Outdoor Center, offering a variety of trails and activities in this pretty setting.
If you’re up for more challenging cycling, you can make a strenuous 8-mile loop from downtown Grafton into the surrounding mountains, featuring stunning vistas and an awesome downhill return to the village.
On your way to Grafton or on your return ride to Bellows Falls, you also have the opportunity to visit the tiny, but charming village of Saxtons River.
This truly unforgettable ride takes you to Chester by way of a tranquil, shaded, unpaved road that follows the course of the Williams River. The beauty of this ride could stand alone, but in addition, this day-trip loop provides the opportunity to visit 3 historic covered bridges and the ever-so-charming village of Chester, with its elongated village green lined with 19th century Victorian buildings, and its good-natured Vermonters looking to share their portion of paradise with you. You’ll definitely want to spend some time exploring Chester’s many artisan and retail shops, and perhaps swing by Chester’s “Stone House Village,” named for the pre-Civil War houses constructed from locally quarried stone.
On your return route to Bellows Falls, you’ll have the opportunity to visit the village of Saxtons River, before your final short stretch of cycling along the Saxtons River.
Rich in variety, this challenging loop takes you immediately across the Connecticut River into New Hampshire, where you will cycle quiet roads through a number of quaint New Hampshire villages, separated by stretches of forests and generally following the course of a rushing stream. Before crossing back into Vermont, you will visit Charlestown, New Hampshire, with its beautifully preserved historic district. You also have the opportunity to visit a restored 18th century fort to experience the early, untamed days of the region’s history.
Back in Vermont, the most challenging part of the route ensues, as the mountains practically fall to the river banks along this stretch. Of course you are rewarded for your efforts with great vistas.
The short ride to Walpole, NH takes you to one of the most charming villages you’ll ever see. Walpole is also home to Burdick’s Chocolates, a true haven for the discriminating chocoholic.
Booking with David saved our vacation! Perfect in every way. I can't recommend David and his services more. This isn't the kind of trip you want to go it alone! David thought of all the details to ensure we had the perfect bike routes and maximized our time. His selection of inns was spot-on -- a variety of properties all different but all special (and with FANTASTIC food and amenities). Can't say enough great things.
We had a terrific Trip! Thank you, David, for the excellent service. The cycling itinerary, accommodations, and dining recommendations were all fabulous. It was a lovely experience and we would highly recommend it!
Wow! David is remarkable! Whatever seemed to go awry, whether a flat, another flat, rain or even support when I had to leave early, David had a back-up plan already developed when he sent a quick reply and made it happen! He was patient, kind and professional at all times. I recommend Diverse Directions Cycling Tours and would select them again in a heartbeat. So glad we found them.
Did a four day cycling trip in Southern Vermont, roughly 30 miles a day, through quaint small towns. We stayed at a charming local inn each night. David, the owner, provided us the routes to follow each day which were super. Roughly half on backroads and the other half on dirt roads which were quiet and picturesque. They collected our bags each morning to transport and were in communication each day with tips, weather and to check-in. We highly recommend to cyclists that love to get out on the bike but don't want to be bothered with logistics, planning the route and don't want to be a part of a group. Was perfect for us!
1547 Route 131
Springfield VT 05156