Looking for the best trails around Rutland?

Explore the best rated trails in Rutland, MA, whether you're looking for an easy walking trail or a bike trail like the East Bay Bike Path (RI) and Mystic River Greenway . With more than 117 trails covering 900 miles you're bound to find a perfect trail for you. Click on any trail below to find trail descriptions, trail maps, photos, and reviews.

Recent Trail Reviews

Chelsea Greenway

trail

January, 2026 by haitaochen363

Good trail

Canalside Rail Trail

Beautiful scenery

November, 2025 by scanlon.gail

The Canalside rail trail is fully open and the paved trail is very well maintained. While it is only 7.2 miles round trip, it’s worth it! Plenty of parking at both ends and the town of Turners Falls has a nice selection of restaurants and shops.

Bruce Freeman Rail Trail

Great country ride, yet close to Urban life

November, 2025 by kleistikow

We’ve biked this many times. It quickly takes you from Lowell, with its National Park, etc to countryside and the center of small towns along smooth, paved, well-maintained trail. Nice to swim in Hart Pond, too, in season, on return trip to Lowell. Trail keeps getting better and better, great facilities along the way as trail is extended.

Accordion

West River Trail (Windham County)

gorgeous fall ride

October, 2025 by darylmarlisa

We started at the marina restaurant at the south end of the trail and rode 3.5 miles on the rail trail section, with another 2 miles on Rice Farm & Quarries roads. Beautiful vistas of the river, rock formations, changing leaves. Esp impressive was the overhead highway bridge built with long tapering multicolored stone supports, representing tree branches. Under the arched stone supports is a picnic table & patio area. A few protruding stones/tree roots need to be managed but biking is very possible on this trail and should be included in the list of options for use.

Washington Secondary Bike Path

Not a bad ride

October, 2025 by trainman1957

This trail needs open parking spaces! Most of the parking spots are blocked off!

East Bay Bike Path (RI)

Where is the bathroom if starting from Providence RI ?

October, 2025 by ningji

don't see bathroom in the parking lot

Monadnock Recreational Rail Trail

A little rough, but good trail.

October, 2025 by toddburrparts

Well, used multiple vehicle vehicles. Maintenance vehicle working on trail . Good views. Will ride again.

Washington Secondary Bike Path

No e-bikes allowed

October, 2025 by dwxchcmrzk

This is a multi use bike trail for everyone to enjoy.

Farmington Canal Heritage Trail

ok

October, 2025 by deceived

Rode a portion from Milldale north to Southington. All paved in fairly decent shape. A few bumps but no broken pavement. At the point in Southington the trail just ends with no information as to where to go. No signs or arrows. The trail picks up somewhere a few miles away but I couldn’t find out how to get there. On the portion I rode it was flat and easy, but not much to see other than woods and backs of buildings.

Upper Charles Trail

lots of street crossings

September, 2025 by chleary11

This is a good trail, but if you start in Milford and do the entire checkmark there are a lot of street crossings. The pretty parts of the trail are nice and shady and wooded, but there is a fair amount of commercial areas that you have to get through. It’s nice and flat and there are lots of parking areas along the way. My gps did not take me to a parking lot but when I put the trail into AllTrails I got accurate directions.

Bruce Freeman Rail Trail

Great ride!!!

September, 2025 by johnbuckley62

Beautiful!

Rockingham Recreational Rail Trail (Portsmouth Branch)

Worth every pedal

September, 2025 by emailforpablo

From Massabesic Lake parking lot to Raymond and back. Beautiful ride. Keep an eye on rocks on the trail. Otherwise, well marked and excellent ride in nature to pretty much all to yourself. Enjoy!

Find Nearby City trails

Accordion

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