102 Things to do near Cheshire, CT
first prev 1 2 3 4 5 6 next lastShowing results within 50 miles Distance miles of Cheshire, CT, USA City, Zip, or Address
Cheshire Lock 12
Cheshire, Connecticut
2.4 miles SA paved hiking, running, and biking path in Cheshire with a small unpaved shoulder — a smooth, accessible multi-use trail for all paces.
Mountain Bike
Brooksvale Park And Naugatuck State Forest
Hamden, Connecticut
3.8 miles SA gateway trail system near Hamden that's great for beginners and opens into the Naugatuck State Forest's awesome singletrack, serious climbs, and plenty of stunts.
Mountain Bike
Panthorn Park
Southington, Connecticut
4.4 miles NA technical but fair wooded layout with a nice balanced mix of holes on fairly level terrain in Southington.
Disc Golf
Flying Ace at Lufberry Park
Wallingford, Connecticut
5.0 miles SEA well-kept free disc golf course in a quaint New England setting with a tight technical front 9 and longer holes with unique elevation on the back — open year-round at Flying Ace in Wallingford.
Disc Golf
Tyler Mills
Wallingford, Connecticut
8.6 miles SEA well-marked network of mostly singletrack trails in Wallingford with small loops, a nice mix of climbs and descents — ideal for intermediates building skills and flow.
Mountain Bike
Farmington Canal Heritage Trail
Hamden, Connecticut
9.0 miles SA smooth, family-friendly rail trail perfect for an easy ride together through Hamden.
Mountain Bike
West Rocks State Park
Hamden, Connecticut
10.6 miles SColor-coded trails in West Rock Park range from a grueling Yellow climb to a flat Red cruise, a White loop around Lake Wintergreen, and a tough Blue that rewards you with direct downtown New Haven views.
Mountain Bike
Middlebury Greenway
Middlebury, Connecticut
11.7 miles WA picturesque walking and biking trail converted from an old trolley bed, rolling through Middlebury with great climbs that singlespeeders especially love.
Mountain Bike
Wadsworth State Park
Middletown, Connecticut
11.8 miles EA hidden singletrack treasure in Middletown between New Haven and Hartford — interesting new singletrack, dual track, and technical sections that pop up unexpectedly at Wadsworth State Park.
Mountain Bike
Page Park
Bristol, Connecticut
12.1 miles NA mostly wooded course with open holes mixed in, a casual stream on a couple of holes, and an OB pond to keep things interesting.
Disc Golf
Larkin State Bridal Trail
Southbury, Connecticut
13.3 miles WA multi-use trail shared by hikers, mountain bikers, cross-country skiers, and equestrians — a popular horseback riding route, so watch your step on the trail.
Mountain Bike
Miller Pond
Durham, Connecticut
14.6 miles ESwim near Durham, Connecticut
Swim
Rockland Preserve
Madison, Connecticut
14.6 miles SEFlowy XC singletrack with berms, log rides, jumps, and volunteer-built features at Rockland Preserve in Madison, Connecticut — including a pump track, a see-saw, and a multi-jump flow line.
Mountain Bike
Thomaston Dam
Thomaston, Connecticut
15.1 miles NWA multi-use area near Thomaston Dam with excellent valley views from the Vista picnic area, fishing along the Naugatuck River, hunting, trailbike and snowmobile riding, and a public model aircraft field.
Mountain Bike
Supply Ponds
Branford, Connecticut
15.4 miles SSteep hills, rocks, and at least one known fallen tree across the trail — a short but physical mountain bike ride that keeps you alert.
Mountain Bike
Genesee Recreation Area
Madison, Connecticut
15.4 miles SEA lightly trafficked mix of access roads and trails on water company land in Madison, Connecticut — good terrain variety and hills for a solid workout.
Mountain Bike
Sessions Woods
Burlington, Connecticut
15.7 miles NA Sessions Woods trail system with a fun mix of rocks and roots, plus connections to nearby areas — road crossings included.
Mountain Bike
Timberlands
Guilford, Connecticut
15.9 miles SEA network of singletrack and forest trails in Guilford — decent variety, though riders report it gets repetitive after a few visits.
Mountain Bike
Middlesex Community College
Middletown, Connecticut
16.0 miles EA sprawling network of singletrack, powerlines, and even a retired motocross track — every skill level welcome, though it's easy to end up 10 miles south if you lose your bearings.
Mountain Bike
Cromwell Creek
Cromwell, Connecticut
16.1 miles NESome good singletrack nuggets remain among the Cromwell Creek trails, though ATV damage has taken a toll — a modest ride worth a visit for local riders.
Mountain Bike
