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Gardner to Keene via North Central + Cheshire Trail (MA, NH-USA)

Quiet and serene side of New England

Easy
Gardner to Keene - 4
Gardner to Keene - 1
Gardner to Keene - 3
Gardner to Keene - 2

Overview

This trail makes for an awesome weekend overnighter (or a very long day for more experienced riders).

This ride stitches together the North Central Pathway (paved town trail from Gardner → Winchendon, MA) with the Cheshire Rail Trail (longer gravel/dirt route through southwestern NH). Together, they form a peaceful cross-state rail-trail experience full of rural scenery, small towns, and classic New England woodland and wetland landscapes. You’ll experience mostly car-free riding with a mix of paved and gravel surfaces that are ideal for gravel, hybrid, or mountain bikes.

The trail is about 50 miles each way, however due to lack of public transit, this will be an out-and-back trail.

Difficulty Explained

This route is considered easy since a large majority is on separated path, there are no serious elevation gains and it is relatively short so the amount of planning will be minimal.

 

Map
Local Amenities
Sites
Logistics
Warnings

Interactive map showing the complete route. Green marker indicates start point, red marker shows the end point.

Local Businesses

Food/Drink

Royal Spice (Troy, NH): Indian Food. . Directly off the trail. 

Lodging
Suggest Local Businesses
Resources

The Cycle Sanctuary (Keene, NH): Primarily a repair shop. . Directly off the trail. 

Notable Sites + Highlights

  • Crystal Lake & Woodland Sections near Gardner and Winchendon — scenic paved trail sections.
  • Small New England towns like Winchendon, Troy, and Fitzwilliam (rail depot history and local charm).
  • Quaint restored train depots and wetlands near Troy.
  • Approaching Keene, NH — a vibrant college town with food and lodging options.

Logistics

Transportation To & From

  • To Gardner: Drive to Gardner, MA — multiple regional connections via Route 12, close to I-190 and I-495 corridors. There is no notable public transit to get here.
  • From Keene: Keene, NH has road access (NH-101, US-12) and lodging/transport options. There are Greyhound buses to get there if you do not have access to car.
  • NOTE: There are no public transit on this trail system, so wherever you park you will need to bike back.

Recommended Gear

  • Bike: Gravel bike or hybrid with wider tires (35mm+) or MTB. Road bike is not recommended.
  • Clothing: Layers, wind/rain gear; trail segments are exposed.
  • Tools: Pump, spare tubes, quick links; roadside repairs likely needed.
  • Electronics: Battery bank, GPX/Map navigation.

Navigation

  • Signage: North Central Pathway well marked; Cheshire trail is also well-marked.  The sections in between are not marked so best to have GPS handy.

Resources Along the Way

  • Food & Water: The only towns on the way which have some notable resources are  Winchendon, Troy, and Keene.
  • Lodging: Keene has the most options (hotels, B&Bs); smaller motels/inns near Winchendon.
  • Phone Signal: Generally good near towns; forested rural sections may see spotty service.

Local Notes

  • Best Seasons: Late spring through early fall for dry trail conditions and moderate temperatures.
  • Permits/Regulations: No permits for rail trails; respect local rules and trail etiquette.

Tips

  • Emergency Number (USA): 911 (+1 country code).

Important Warnings

Not fully signed between trails: Connections between the North Central Pathway and Cheshire Rail Trail are not always clearly signed
Trail gaps: North Central Pathway has small on-road gaps and is not yet fully connected between towns
No bike shops on trail except for in Keene, NH so definitely have some spare tires and a pump at a minimum.

Route Details

Distance(Miles)

104 mi

Duration

1-2 Days

Elevation(ft)

2000

Countries

United States

Start/End Points

Gardner, MA -> Walpole, NH

Route Format

Point to Point

Bike Lane Types

Bike Path
80%
Separated Bike Lane
0%
Shared Lane
20%

Tags

Fall ColorsForestRail-TrailScenic

External Resources

  • Cheshire Rail Trail community details
  • North Central Trail - BikeitorHikeit
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