Looking for the best trails around Milford?

Explore the best rated trails in Milford, CT, whether you're looking for an easy walking trail or a bike trail like the Windsor River Trail and Niantic Bay Boardwalk . With more than 71 trails covering 562 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

Harlem Valley Rail Trail

Everything you could ask for

October, 2024 by robert.richter89

I rode the entire 24.7 mile southern portion of the Harlem Valley Rail Trail on a beautiful fall day. The HVRT offers everything you could want from a trail experience: a fully paved surface, mostly flat, beautiful scenery (especially in the Fall) and a perfect mid-point trailhead to grab a bite to eat.

I don't recall seeing any water fountains along the trail although the trailhead in Millerton offers many options for places to eat or resupply. The HVRT offers a myriad of scenery changes from farmland, quiet streams, distant hills to quaint towns. I have ridden many paved rail trails in the past and the HVRT is one of the best with almost no surface imperfections for the entire distance. There are many trailheads along the entire trail giving many distance options. All this adds up to a perfect trail in my opinion!

Harlem Valley Rail Trail

trail is complete now but map not updated

October, 2024 by vbergerg_tl

Map is 6 months out of date

Vanderbilt Motor Parkway

Ride from Alley Pond to Citifield

October, 2024 by peterosenrosen@gmail.com

This trail continues 8 miles from Alley Pond Park all the way to Flushing Meadows Park, home of the 2024 World Series champion NY Mets! You only have to cross 3 streets for the entire ride. You continue past Cunningham park to peck fields then to Kissena Park, Kissena Corridor Park, then alongside the Queens botanical garden. It’s pretty flat, nicely paved, and you can safely ride it at night. Leave your

Accordion

Old Erie Path

Good Connector Trail

October, 2024 by cehersh

We recently did a loop ride, crossing the George Washington Bridge and Mario Cuomo Bridges. This trail was a seamless connector from Rt. 9 and the town of Sparkill to the MCB. It's fairly narrow with occasional views across the Hudson River and the bridge. The condition was pretty good, gravel/dirt.

Bronx River Greenway

A Bit Disjointed

October, 2024 by cehersh

We attempted to ride the entirety of the greenway in two halves, north and south. North have was pretty good--a lot of raised roots on pavement--from Valhalla and south to Bronxville. The southern half began with an abrupt dead end below Bronxville, followed by miles on road. We eventually linked up with a bike lane alongside roadways that led us as far south as Bronx Zoo. Overall, the trail lack good markings and directives. We were disappointed with the southern section of greenway and aborted plans of continuing to the East River. Wanted to like it!

Cheney Rail Trail

Cheney Trail

September, 2024 by nicoleh742

Hubby and I discovered this trail last fall. We absolutely love it. It's a beautiful hike with all the leaves changing. Great for pets too as it's a pretty flat walk. It's def longer than 1.7 miles though. I love that the leaves are changing we will be frequented this trail alot during this fall season!

Cheney Rail Trail

Cheney Trail

September, 2024 by nicoleh742

Hubby and I discovered this trail last fall. We absolutely love it. It's a beautiful hike with all the leaves changing. Great for pets too as it's a pretty flat walk. It's def longer than 1.7 miles though. I love that the leaves are changing we will be frequented this trail alot during this fall season!

Setauket-Port Jefferson Station Greenway Trail

Great path but the abandoned warehouse is gone so seeing old building aspect gone, and they are not maintaining with the roots pushing up the road

September, 2024 by jrfarrell1991

Great path but the abandoned warehouse is gone so seeing old building aspect gone, and they are not maintaining with the roots pushing up the road

William R. Steinhaus Dutchess Rail Trail

Hopewell Junction

September, 2024 by flywithme_tl

Went from the Thuway area in Poughkeepsie over the walkway and ride to Hopewell junction .Nice trail well groomed , paved not much to look at but very cool what the volunteers did to the RR depot , signal house and pavilion, the depot museum was great . Went to Daddy O’s restaurant on the trail , good food . The NY empire trail continues along live tracks goes I believe quite far .

Air Line State Park Trail

We had a great ride! 6.6 miles. Beautiful day!

September, 2024 by susanmazur13

We had a great ride! 6.6 miles. Beautiful day!

Westchester RiverWalk (Croton-on-Hudson)

great trail!

September, 2024 by ymm10501

Super calm,people are kind, and a great way to relax!!

Bethpage Bikeway

Great ride

August, 2024 by f9rys6884g

Biked the entire run, from Woodbury to Massapequa. Completely paved path the entire way. Only half-dozen “small bumps” along the entire way due to tree roots, but seriously, nothing to complain about.

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