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If you live in or near Greenwich, you don’t have to travel far for a great ride. We've put our heads together and compiled a guide of nearby rides to explore. All within an hour or so, you’ll find bike-friendly trails that range from paved paths to stone-dust rail-trails to rugged single-track. These are real riding destinations - a great opportunity to expand beyond shorter loops.
Here are four excellent options. All are officially open to bikes, each has its own character, and all make for a worthwhile day trip from Greenwich.
Length: ~20.8 miles one way
Surface: Crushed stone, packed earth
Best for: Gravel or hybrid bikes, casual road bikes with wider tires
The Hop River State Park Trail follows a former railroad corridor from Manchester to Willimantic. The surface is mostly stone dust, which makes it friendly for hybrids, gravel bikes, and even mountain bikes. Road bikes can ride most sections, though some areas are bumpier and better with wider tires.
From Manchester to Andover, the surface is smooth and shaded, perfect for a steady pace. Beyond Andover, you’ll find more rustic sections with some rougher ballast. It’s a quiet, scenic ride through forested cuts, farmland, and over small bridges.
Hop River is also part of the East Coast Greenway. It connects with other trails in the region, so you can extend your day if you want more mileage.
Length: ~17 miles in Cheshire and Hamden (part of a much longer corridor)
Surface: Paved
Best for: Road bikes, hybrids
This is one of the smoothest rides you’ll find in the state. The Farmington Canal State Park Trail runs about 17 paved miles between Cheshire and Hamden. It’s part of the larger Farmington Canal Heritage Trail, which stretches through many towns and into Massachusetts.
The gentle grade makes it easy for riders of all levels. It’s ideal for road cyclists who want a safe, car-free training ride, as well as families looking for an easy day out. Along the way, you’ll pass historic canal features like Lock 12, shady greenways, and well-kept neighborhoods.
With frequent benches and parking areas, it’s easy to start or stop wherever you like. A newer section in New Haven connects more neighborhoods to the trail, making it even more useful for both commuting and recreation.
Length: ~ 7 miles of interconnected trails
Surface: Natural dirt singletrack with roots, rocks, and bridges
Best for: Hardtail mountain bikes or front-suspension hybrids
For a smooth introduction to backcountry riding, Mianus River Park delivers. The terrain ranges from flat riverside stretches to gentle rolling hills, with a few rooty sections for variety. Most trails are wide enough to ride side-by-side with a child, making this an excellent option for families. Dogs, hikers, and joggers also frequent the area—so be prepared to share the trail.
The main loop offers a comfortable ride for youth and casual cyclists, but there are a few side spurs with tighter turns and more elevation for riders looking to level up. The flow is natural, and the forest canopy provides shade even in the heat of summer. You can easily spend a few hours here and still have more to explore.
Gear Tip: A hardtail mountain bike is more than enough. Parents should consider wider tires for stability and a basic suspension fork for comfort on roots and gravel.
Length: ~4.5 miles one way
Surface: Paved
Best for: Families, casual riders, scenic spin
The Windsor Locks Canal Trail runs along the Connecticut River between Suffield and Windsor Locks. The path follows a historic canal towpath, giving you water views on both sides — the river on one, the canal on the other.
It’s flat, paved, and very accessible. This makes it an excellent choice for families, beginner riders, or anyone who just wants a relaxed, scenic ride. The quiet setting is great for spotting herons, egrets, and sometimes bald eagles.
At 4.5 miles one way, it’s not a long ride, but an out-and-back gives you about nine miles of easy pedaling. It’s also a good warm-up or cool-down if you’re linking it with nearby road riding.
Length: ~5 miles of single-track (loop options available)
Surface: Dirt, roots, rocks, technical features
Best for: Intermediate to advanced mountain bikers
If you want a change from rail-trails and pavement, Graham Hills Park delivers. Located in Pleasantville, NY, just over the Westchester border, this is a true mountain-bike destination. It offers about five miles of marked single-track, with loops and connectors that can add mileage.
The trails here are technical — expect roots, rocky drops, tight turns, and challenging climbs. There are also optional features for riders who want to test their skills. A proper mountain bike is essential, along with a helmet and gloves.
Because it’s mostly wooded, the park stays cooler on hot days. Riders use it for both quick after-work laps and longer weekend sessions. Its proximity to Greenwich makes it an easy go-to spot for dirt riding.
Hop River State Park Trail – Best for long, steady rides on crushed stone.
Farmington Canal State Park Trail – Best for smooth, paved riding without traffic.
Windsor Locks Canal State Park Trail – Best for short, scenic rides and families.
Graham Hills Park – Best for technical mountain biking close to home.
Travel time: Most of these trails are within 45 minutes to 1.5 hours.
Parking: Use the official park links above for parking locations.
Bike choice: Match your bike to the surface — hybrids and gravel bikes for stone dust, road bikes for pavement, mountain bikes for Graham Hills.
Weather: Stone dust can be soft after rain; technical trails can be muddy.
Bring supplies: Water, snacks, and layers, especially for longer rides.
These four trails give you variety without the need for an overly-long trip. You can cruise crushed stone for miles, glide on pavement, take in river views, or push your limits on technical single-track.
From the peaceful Windsor Locks Canal to the challenging loops of Graham Hills, there’s something here for every type of rider. Pick the one that fits your mood and get rolling — the best rides near Greenwich are closer than you think.
