About this Itinerary
The Cheshire Rail Trail is a quintessential New England experience, providing 33-miles of beautiful scenery and charming villages with a varied terrain that makes it the perfect trail in any season. Once the route of the Cheshire Railroad, which ran from 1848 to the early 1960s, today’s trail covers only a section of the former rail route. The railway brought passengers who came to hike nearby Mt. Monadnock (notable visitors include Henry David Thoreau and Ralph Waldo Emerson), as well as being integral to the transportation of granite from several quarries in the region. Today, you will see only remnants of the former railway as you pass through towns for which the railroad was once the lifeblood of the region. Now, the former rail corridor provides visitors with varied interests, such as biking, hiking, horseback riding and cross-country skiing, with the opportunity for a fun adventure.
Located in southwestern New Hampshire, the CRT travels north from the Massachusetts border through the small college town of Keene and ends at the southern outskirts of Walpole. While very enthusiastic riders might consider completing this trail in one day, our itinerary covers the trail in a leisurely two days. Bike rentals are not available in the area. The closest rental shop is Brattleboro Bikes in Brattleboro, Vermont, about a half hour drive from Keene. Approximately an hour and 15 minutes away in Nashua, Goodales Bike Shop rents a variety of bikes, as well as carriers for your car, if that is needed.
At almost exactly the halfway point along the CRT, Keene provides the perfect base from which to bike the northern section of the trail one day and the southern section the next. Founded in the mid-1700s, this former mill town has preserved a great number of its historical buildings, contributing to what The National Trust calls a “Currier & Ives landscape.” The downtown area in particular has seen revitalization in recent years and visitors will enjoy strolling around the town square and admiring the many beautiful Colonial and Victorian-era buildings.
In the downtown area, stay at The Colony House, a historical property located within easy walking distance to restaurants, parks, the theater, and shops. Built in 1819, and now listed on the National Register of Historic Places, the property is recognized as one of the most significant federal style buildings in the state. Each of the four rooms has a private bath, a kitchenette is available for guest use, and a full breakfast is included each morning.
On this itinerary we head northeast for the first day of biking, but the route could easily be done in reverse. There are a very limited number of trailheads on the ‘upper’ section of the CRT, and there are no opportunities to replenish water, so it is necessary to pack everything you need. Before departing, stop by Kristin’s Bistro & Bakery, voted one of the best bakeries in New England, to pick up a fresh gourmet sandwich or spinach filled croissant. The shop is located a short walk from The Colony House on Washington Street. On Central Square, Luca’s Market offers a wide range of Mediterranean inspired sandwiches and salads. Be sure to try their fresh homemade mozzarella. Why not plan ahead for a sugar craving and fill out your pack with homemade sea salt caramels, orange creams, coconut clusters or artisan truffles? Life is Sweet Candy and Cupcakes, also located on Central Square, features a seemingly endless selection of sweets to tempt even those who claim not to have a sweet tooth.
The trailhead for the northern section of the CRT is less than a half mile from Colony House. Take a left on School Street and a left through the parking lot immediately after Gilboa Avenue. Look for the trailhead across Island Street. The portion of the trail within Keene is paved, but, as you leave town behind, the route changes to dirt and gravel and riders have noted that some sections can be difficult due to damage from ATVs.
There are no off-trail diversions on this section of the CRT, but you will enjoy a peaceful ride through a thickly forested corridor. Look for birds such as the northern cardinal, scarlet tanager and blue jay hiding in trees or hawks and osprey soaring overhead. The trail ends at the intersection with Bookseller Road and Route 12. If you are on the trail from August through October, stop by Alyson’s Orchard (just past the end of the trail on Route 12.) Here you will find freshly picked apples, as well as baked goods and other locally produced products. Alyson’s also has lodging available in two farmhouses and a restored barn located on the property.
Upon your return to Keene, stop by Elm City Brewing Company for a refreshing pint of Peachy Keene Kolsch, Monadnock Mt. Ale, Pothole Porter or another of their freshly brewed beers and a savory appetizer or delicious burger. Located in the restored Colony Mill Marketplace, the brewery is ideally situated at the end of the bike trail.
To reach the southern section of the CRT from Colony House, take a left on School Street and look for the entrance on the right immediately past Gilbo Avenue. This section of the trail is new and does not connect all the way through town (though plans are in place to eventually connect the entire trail through Keene). When the trail ends, bear right at the police station on to Marlboro Street. Follow this road for a short way until it intersects with NH-101E and look for the trailhead across the street. The section on the road is minimal and traffic is light, although riders should be cautious crossing NH-101.
The beginning of this section of the CRT is sandy, but soon changes to packed dirt as you head toward the town of Troy. The small town is marked by a beautifully restored 1847 train depot with documents and artifacts that chronicle the history of the railroad that once passed through. Unfortunately, there are no public viewing hours, but private tours can be arranged in advance.
If you find yourself on the CRT in mid-July, don’t miss the Rhododendron State Park. Located off the Rockwood Pond intersection, this 16-acre grove of rhododendron maximum, is simply spectacular when in bloom. A 0.6-mile-long trail encircles the grove allowing for an up-close look and smell of the flowers. The grove, which is the largest in northern New England, is a designated National Natural Landmark. Restroom facilities are available.
On a hot day, stop for a quick swim at Rockwood Pond, a popular local spot for cooling off. As you ride along, the trail passes through evergreen woods, ponds, swamps and wetland areas. On a clear day, this section offers spectacular views of Mt. Monadnock in nearby Jaffrey.
The CRT continues to the town of Fitzwilliam, a picture postcard New England village with a town common surrounded by 12 homes on the National Register for Historic Places. Built in 1796, the Fitzwilliam Inn was a stop on the old coaching road between Boston and northern parts of New England. The perfect place to have lunch, the Inn’s pub serves sandwiches, burgers and pizza in a casual setting. Be sure to spend time exploring the common rooms of the property to learn more about the town’s history. Also visit the Fitzwilliam Historical Society, located across the street in The Amos J. Blake House. This building was constructed in 1837 as a store and living quarters by the Blake family and donated to the Historical Society. Take a tour of the building and visit the attached country store, which features items made by local artisans.
The trail continues just a little past the town of Fitzwilliam and ends at the Massachusetts border. Head northeast from here and enjoy a leisurely return to Keene. Once back in town, take a slight diversion to Piazza Ice Cream. Featuring soft serve, yogurt and hard ice cream in a variety of flavors such as LL Bean’s Muddy Boots, Orange Pineapple, and Maine Lobster Tracks. To reach the shop, turn left off the trail at the Water Street intersection in town and take the second right onto Main Street where the shop will be on your left. To return to the trail, continue down Main Street, turn left on Commercial Street, take a quick right on St. James Street and you will enter one block from the end of the CRT.
If you’re hungry upon your return to Keene, check out The Stage American Bistro, located on Central Square in the heart of town, which features a varied menu from classic comfort food to more adventurous dishes such as Bohemian Bouillabaisse. Also known for their creative cocktail menu and homemade desserts, there is something for everyone at this busy bistro.
Or, after a long day of biking, enjoy a delicious meal and a glass of fine red wine at Luca’s Mediterranean Cafe. With a relaxing atmosphere and a wide variety of Mediterranean dishes, Luca’s is one of the most popular spots in town. Next door to the restaurant is Luca’s Market; featuring prepared foods and sandwiches, the market is the perfect place to pick up lunch to go.
If you have an extra day to spend in the area, there is much to explore. Start with the Horatio Colony House Museum, an 1806 Federal-style house that was the home of Horatio Colony II, a descendent of one of Keene’s most prominent industrial families and relative of a former owner of The Colony House. The museum features original furnishings and decorative arts just as when the family lived there and provides insight into life from this time period. Also on the grounds is a nature preserve with plants that were originally planted by Mr. Colony.
Visitors have been coming to the region for decades to hike Mt. Monadnock. Reputed to be the second most hiked mountain in the world after Mt. Fuji in Japan, no visit to the area is complete without hiking to this popular peak. The word ‘monadnock’ comes from the Abnacki tribe and means ‘mountain that stands alone.’ With no other mountains nearby and a treeless summit, the views from the peak stretch far into the distance and hikers can see mountain ranges in Vermont and Massachusetts on a clear day. At just over 3,000 feet, the mountain is not especially high, however, its fine views, boulders and big rock slabs make this a fun family-friendly adventure.
For covered bridge enthusiasts, southwest New Hampshire is the perfect place to explore back roads as the region has seven covered bridges. Take a road trip to explore these quintessential New England structures and visit some of the charming small towns clustered throughout this part of the state. Follow this guide to visit all seven of the beautifully preserved bridges in the Monadnock Region.
Ready for more biking? Keene is fortunate to have another rail-trail, the Ashuelot Rail Trail, which travels more than 21 miles from Nashua to Hinsdale. Another dirt trail, the route crosses covered bridges, passes through historical towns and offers spectacular scenery. Look for the trailhead near Keene College.