4 New England States in 3 Days

Follow old canal and rail corridors north through college towns, farm valleys, and the Connecticut River, crossing state lines until you roll into a Vermont river town.

Distance
132.2 miles
Surface
95% paved
3 days–1 week
Route Type
Point to Point

Ride the 4 New England States in 3 Days

Leave New Haven on the Farmington Canal Heritage Trail and ride north through the Pioneer Valley and up the Connecticut River to Brattleboro, Vermont. Amtrak serves both ends.

What to Expect

A three-day linear tour with more than half its distance on rail-trail corridors and enough road connections to keep the ride varied. Mostly gentle grades make the mileage approachable for experienced touring riders, though the remaining trail gaps require attention.

Crossing Connecticut, Massachusetts, New Hampshire, and Vermont in one compact trip is the obvious hook, but the continuous thread is the old canal-and-rail corridor. New Haven, Northampton, and Brattleboro provide strong cultural bookends and overnight energy.

The route covers 132.2 miles and gains about 4,400 feet. Much of the ride follows paved rail-trails, with rolling roads and unfinished gaps around Plainville and elsewhere. Expect wooded trail corridors, historic mill towns, broad farm fields in the Pioneer Valley, and river views along the Connecticut.

Towns and services are regular, particularly around New Haven, Avon and Simsbury, Northampton, and Brattleboro. Some rail-trail portions have limited immediate water or repair options, but the route never becomes truly remote.

Late spring through early fall is best. Summer can be hot and humid, spring brings rain and soft shoulders, and autumn offers crisp temperatures with shorter days. Northern sections cool quickly after sunset.

Plan Your Ride

Divide the ride into three days around indoor lodging, reserve train bicycle space, and use the current digital route through the unfinished Plainville gap.

Trip Planning & Logistics

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Amtrak serves New Haven and Brattleboro, but bicycle reservations and loading procedures depend on the train, so verify them while booking. The Farmington Canal Heritage Trail still has an unfinished gap in Plainville, where the route uses streets. Download the current Ride with GPS route, and confirm construction or detours before travel.

A touring, hybrid, gravel, or road bike with tires around 32 millimeters or wider is appropriate. Bring lights for road gaps and tunnels, rain layers, a lock, and normal multi-day repair supplies.

Indoor lodging is the simplest option and is available near the likely overnight areas. Camping exists in the broader corridor but may require detours and advance reservations, so confirm each site before building an itinerary around it.

Full services are available in the major towns, with cafes and markets in smaller communities along the way. Carry snacks and water for longer greenway stretches, and refill whenever convenient.

Use care on the Plainville road gap and other unfinished connections. Trail crossings, urban streets, wet leaves, and changing construction are the main concerns. Check current Amtrak rules and trail alerts before departure.

Routes change. Bridges wash out, businesses close, and construction pops up overnight. We strive to keep routes updated as those things happen. When we learn about a change, we reroute around sections that have become dangerous or are temporarily closed for road work, bridge outages, or construction, and we update service information as businesses open, close, or move. Digital routes are updated as soon as we’ve reviewed a reported issue.

You’re often the first to spot these changes out on the road. Help us keep this route accurate for the next rider by reporting anything you notice with our Route Feedback Form.

This Route Is Part of a Community Effort

Short Routes are cyclist-submitted and Adventure Cycling approved, with the mission of inspiring more adventures from your own backyard. All possible thanks to the dedicated support of our members and donors.

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Frequently Asked Questions

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A collection of free, cyclist-submitted routes built for shorter trips. Each route is designed for a trip of one to five nights, ranging from a quick overnight ride to a longer multi-day adventure. It’s the most accessible of our three route networks: no purchase required, no advanced experience assumed, just a well-vetted route you can ride over a weekend or a week off.

We launched Short Routes in August 2022 with an initial set of 12 routes, created specifically because our epic, long-distance routes don’t work for everyone. Someone with a week of vacation, or someone new to bike touring, needs a different starting point. We developed that first collection in partnership with BIPOC, LGBTQ+, women, and intersex cyclists, with routes centered near major cities like Los Angeles, Seattle, Minneapolis, Austin, Atlanta, Washington, D.C., Philadelphia, and Boston, so people could find a route close to home rather than needing to travel somewhere remote first. Since then, the collection has grown through rider submissions and partnerships with other organizations like East Coast Greenway Alliance.

It’s the only one of our three networks built primarily by the community, for the community. Typically, the route builder is local to the area, providing special knowledge about transportation logistics, services, points of interest, and more. Anyone can submit a route, but every submission goes through a staff review: checked for traffic speeds, shoulder width, surface conditions, and whether services like food, water, and camping are realistically spaced for a loaded touring bike.

Riders who don’t have weeks to spend in the saddle, and riders who’ve never done a multi-day bike trip before. The collection was built with input from locals and includes routes near major cities, so that cyclists who live far from the endless miles of gravel roads or remote bikepacking routes have great routes mapped near them.

No. Many of our Short Routes are built to be beginner-friendly, though all are worth riding no matter your experience level. Because each one runs just one to five nights, it’s a much lower commitment than a cross-country tour, which makes it a good place to start if you’ve never done a multi-day ride.

Anyone can submit. You don’t need any official affiliation with Adventure Cycling. Head to our route submission form, and come prepared with three things: at least 10 photos from the route, a written description covering the highlights, navigation notes, services along the way, seasonal considerations, and a short bio about you as the route’s creator, and a Ride with GPS route that includes automatic cuesheetsand custom points of interest for things like lodging, food, bike shops, and any hazards.

It needs to take a beginner one to five nights, cover 50 to 200 total miles, and be located anywhere in the U.S. or Canada. Beyond that, we’re mainly checking for safety. A route can’t put a fully loaded touring cyclist through excessive hazards, so we look at things like traffic speed, shoulder width, road surface, and whether food, water, and camping are realistically spaced along the way.

It helps if you rode it within the past year or so. Those submissions move through review faster, since conditions on the ground are more likely to still match what you’re describing. Older routes can still be submitted, but they may take longer to review since we may need to double-check that services and conditions haven’t changed.

Review typically takes several weeks. We check every submission for safety and accuracy and reserve the right to edit before publishing. If your route is approved, we’ll follow up with you by email.