Explore the best rated trails in Smithtown, NY. Whether you're looking for an easy walking trail or a bike trail like the Norwalk River Valley Trail and Ridgefield Rail Trail. With more than 68 trails covering 437 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.
The Jones Point Path occupies an abandoned motor vehicle route (old US Route 9W). The path provides bicyclists with a relatively safe bypass to a dangerous section of busy US Route 9W near Bear...
The former “Old Put” commuter rail corridor that ran from the Bronx to northern bedroom communities in Westchester and Putnam Counties is popular once again, only this time it’s for people riding...
The Laurelton Greenway is a short but well-maintained multiuse path connecting the neighborhoods of Jamaica and Rosedale in southern Queens, NY. The two-lane paved trail starts in Jamaica, and travels...
When complete, Connecticut’s Shoreline Greenway Trail will be a scenic 25-mile route through four quaint New England towns off Long Island Sound. From Lighthouse Point to Hammonasset Beach State Park,...
The Qunnipiac Linear Trail is an easy multipurpose path in Wallingford, Connecticut. The trail skirts Community Lake while traveling a heavily wooded corridor along the Quinnipiac River. It is one of...
Like Wantagh State Parkway, Ocean Parkway was built in the postwar 1930s to provide access to the crown jewel of the state park system, Jones Beach State Park. Unlike the former road, however, this...
The North Shore Rail Trail, formerly known as the Rails to Trails Recreational Path, is a 10-mile multi-use recreational path and runs along the former Wading River railway corridor in Brookhaven—the...
The two diverse sections of the Shore Parkway Greenway Trail blend urban and scenic, offering views of sights ranging from the Statue of Liberty to wildlife refuges. Following the Belt/Shore Parkway,...
The Hudson River Waterfront Walkway is a 1.5 mile walkway along the bank of the Hudson River in Jersey City. The walkway offers stunning views of Manhattan as well as access to a number of ferries and...
First a canal, then a railroad, and now a trail define the history of the Farmington Canal Heritage Trail. Completed segments span Connecticut south to north, from New Haven to the Massachusetts...
The 3.1-mile Kress Family Trail in Roxbury occupies the former route of the Shepaug Valley Railroad (the Shepaug, Litchfield and Northern Railroad). The railroad was famously known as the “crookedest...
Although just a mile long, the Beach Channel Drive Greenway in Queens offers expansive views of Jamaica Bay and the beautiful Marine Parkway Bridge as it traces the border of Jacob Riis Park. On the...
Roosevelt Island Greenway, a little-known gem in the Big Apple, was named after President Franklin Delano Roosevelt in 1973. To reach this scenic pathway, board New York City’s only aerial tram,...
The Mosholu-Pelham Greenway connects several parks and recreational opportunities in New York City's north and central Bronx neighborhoods. A portion of the trail is also part of the growing East...
When completed, the Norwalk River Valley Trail will run from Danbury to Long Island Sound in southwestern Connecticut, for a total of about 27 miles. Currently, several disconnected sections totaling...
The Jones Beach Boardwalk traverses Jones Beach State Park, running parallel (and south of) Ocean Parkway. The pleasant pathway offers views of the beach and the ocean. Although bicycles are...
The Sandy Hook Multi-Use Pathway travels 8.7 miles alongside the picturesque beaches and historical monuments of the Sandy Hook peninsula. The pathway begins in the Gateway National Recreation Area...
Closure Notice: As of 2021, the city is undertaking a series of construction projects in East River Park, which will result in ongoing closures to sections of the southern segment of the greenway...
The Hutchinson River Greenway offers a convenient alternative to the Hutchinson River Parkway, which it closely follows. Although adjacent to the busy thoroughfare, trees have been planted along the...
Note: As of December 2021, the trail is fully complete except for a bridge on its southern end in Brewster; stairways on either side of the bridge are available for the detour. Construction on the...
The old New York Central rail line that ran from the Bronx to northern bedroom communities in Westchester and Putnam Counties carried commuters during the workweek, but on the weekends tourists...
At first glance, there’s no evidence that an aqueduct ever existed along the Old Croton Aqueduct Trail. The trail is often a singletrack dirt pathway that winds through communities and trees and...
The Briarcliff-Peekskill Trailway is a 12-mile linear park that runs from the town of Ossining north to Westchester County's Blue Mountain Reservation in Peekskill. The trail is built on land...
The Eastern Parkway Trail is a 2-mile route along a tree-lined boulevard in Brooklyn's Crown Heights neighborhood. The path begins at Prospect Park, which houses some of Brooklyn's most popular...
While not a "rail-trail," the Hook Mountain/Nyack Beach Bikeway is a very scenic trail along the Hudson River in Rockland County. The southern half of this trail is flat and runs right along the...
The Larkin State Park Trail meanders 10.8 miles through the woods and around the lakes and low hills of southwestern Connecticut. The rail-trail follows the route of the New York & New England...
The Hanover Pond Trail is a mile-long rail-trail in Meriden, Connecticut offering scenic natural escape combined with historical exploration. The smooth asphalt trail is open to a diverse range of...
Tallman Mountain State Park Bike Path is partially paved and bisects the Tallman Mountain State Park. The route provides a motor-vehicle-free way for bicyclists using US Route 9W to connect with...
The Hutchinson River Greenway offers a convenient alternative to the Hutchinson River Parkway, which it closely follows. Although adjacent to the busy thoroughfare, trees have been planted along the...
The EPCAL Alternative Transportation Path loops around the 2,900-acre Enterprise Park at Calverton (hence its name: EPCAL) on New York’s Long Island and links to the Town of Riverhead’s 65-acre...
The two diverse sections of the Shore Parkway Greenway Trail blend urban and scenic, offering views of sights ranging from the Statue of Liberty to wildlife refuges. Following the Belt/Shore Parkway,...
The Franklin D. Roosevelt Boardwalk follows Staten Island's eastern shore from Miller Field -- a recreational area for sports, picnicking and bird watching -- to Fort Wadsworth. Highlights of the...
The John Kieran Nature Trail is a short loop that borders Van Cortlandt Lake and its associated wetlands. It is a wonderful site for bird-watching. The trail also passes several sites of significance...
The Setauket-Port Jefferson Station Greenway Trail stretches just over 3 miles along Long Island’s north shore. Construction was completed in two phases with the first trail section opening in 2009...
The nicely paved Bethpage Bikeway runs alongside suburban roads for long segments of the route, but it’s much more than a suburban trail. Each on-road suburban stretch is broken up by one of three...
Randall's Island Park Trails offer a series of interconnected paved loops on an island in the New York City borough of Manhattan. The park offers a quiet setting, especially enjoyed by runners, with...
Although just a mile long, the Beach Channel Drive Greenway in Queens offers expansive views of Jamaica Bay and the beautiful Marine Parkway Bridge as it traces the border of Jacob Riis Park. On the...
The Fort Washington Park Greenway brings residents and visitors to Washington Heights right up to the edge of the Hudson. The mile-long trail begins near the pier at the end of Dyckman Street and...
A former right-of-way of the NY & NJ Railroad. Near historical Mount Ivy which was the center of a Quaker settlement in the 18th century. Hiking along railroad bed and wildlife observation and...
The Kings Park Hike & Bike Trail runs for 1.5 miles between Old Dock Road at Church Street in Kings Park and Nissequogue River State Park. The trail is a town of Smithtown park and follows an...
The Eastern Parkway Trail is a 2-mile route along a tree-lined boulevard in Brooklyn's Crown Heights neighborhood. The path begins at Prospect Park, which houses some of Brooklyn's most popular...
The Franklin D. Roosevelt Boardwalk follows Staten Island's eastern shore from Miller Field -- a recreational area for sports, picnicking and bird watching -- to Fort Wadsworth. Highlights of the...
The Sandy Hook Multi-Use Pathway travels 8.7 miles alongside the picturesque beaches and historical monuments of the Sandy Hook peninsula. The pathway begins in the Gateway National Recreation Area...
The Jack Harrington White Plains Greenway was recently renamed to honor a long-time member of the city's conservation board. The trail's corridor follows the former New York, Westchester & Boston...
The Raymond G. Esposito Memorial Trail travels from one end of the village of South Nyack to the other in 1 mile but greatly expands its reach by connecting with the Old Erie Path and a new shared-use...
The Briarcliff-Peekskill Trailway is a 12-mile linear park that runs from the town of Ossining north to Westchester County's Blue Mountain Reservation in Peekskill. The trail is built on land...
The Hudson River Waterfront Walkway is a 1.5 mile walkway along the bank of the Hudson River in Jersey City. The walkway offers stunning views of Manhattan as well as access to a number of ferries and...
The Old Erie Path reveals spectacular views of the Hudson River Valley as the rail-trail rolls along cliffs that border the river’s western shore. Although fairly short, it joins two other...
When complete, Connecticut’s Shoreline Greenway Trail will be a scenic 25-mile route through four quaint New England towns off Long Island Sound. From Lighthouse Point to Hammonasset Beach State Park,...
While not a "rail-trail," the Hook Mountain/Nyack Beach Bikeway is a very scenic trail along the Hudson River in Rockland County. The southern half of this trail is flat and runs right along the...
Roosevelt Island Greenway, a little-known gem in the Big Apple, was named after President Franklin Delano Roosevelt in 1973. To reach this scenic pathway, board New York City’s only aerial tram,...
The Hutchinson River Greenway offers a convenient alternative to the Hutchinson River Parkway, which it closely follows. Although adjacent to the busy thoroughfare, trees have been planted along the...
When Jones Beach State Park opened on Long Island’s South Shore in the late 1920s, a series of scenic parkways was built on infill dredged from nearby towns to connect New Yorkers to the new public...
You might expect a 4-mile rail-trail that passes through three downtowns to be excessively urban, but the quaint town centers on the Joseph B. Clarke Rail Trail are compact and surrounded by...
The Kennedy Trail begins at Brick Hill Road and ends at the northwest corner of the 68-acre campus of John F. Kennedy Catholic High School in Somers. The cinder trail, built on a former rail bed,...
Tallman Mountain State Park Bike Path is partially paved and bisects the Tallman Mountain State Park. The route provides a motor-vehicle-free way for bicyclists using US Route 9W to connect with...
Although just a mile long, the Beach Channel Drive Greenway in Queens offers expansive views of Jamaica Bay and the beautiful Marine Parkway Bridge as it traces the border of Jacob Riis Park. On the...
The Bronx River travels from the mouth of the East River north to the Kensico Dam, providing views of the natural history of the area. Because the trail is under development, there are several gaps...
The Middlebury Greenway provides a paved, off-road option for a self-propelled journey across suburban Middlebury. The trail touches on several business districts and parks, ending at an amusement...
The Ocean Parkway Trail closely follows its eponymous thoroughfare nearly 5 miles through several Brooklyn neighborhoods, ending only a block from the popular Coney Island boardwalk. Those traveling...
This trail is a good idea in terms of riding from Van Cartland Park to City Island. The execution however leaves a lot of room for improvement. The mostly asphalt paths are in rough shape -cracked, tree trunk and root damage, in need of lane markings both to designate the trail and to help keep people in the proper lanes (a big issue considering the number of walkers using this trail). There are signs to help navigate this trail but they are busy and difficult to read for bikers and could be more prominent as it’s easy to miss turns at intersections.
Although a bit narrow given the amount of use this trail gets the paved surface is smooth. Nice addition to the Empire State trail joining the south county to other trails in the area.
The Maybrook has quickly become one of our favorite rail trails. Basically brand new, uncrowded, lots of interesting sights along the way including multiple water views and lots of greenery.
Today we rode from the Brewster trailhead at Lake Tonetta both ways: Out and back to the CT line, and then out and back in the other direction up past the Ice Pond, for a total of about 20 miles. The first segment to the CT line was new to us; there is an on-road detour due to a bridge out at Peaceable Hill Road. You walk down a flight of steps, ride down Peaceable Hill Road to Rt. 6, turn left on Rt. 6, go down the hill, turn left again on Rt 6 and then ride up the hill past the Honda dealership where another set of stairs on the left will bring you back to the trail. These stairs are fairly steep but it can be done. The road has a shoulder but is a bit busy; experienced road riders will find this easy to navigate, others can simple walk along the sidewalk. Your reward is that the other end of the trail as you ride east is a very nice section past East Branch Reservoir, including a long section right along the water. One way mileage is about 5 miles, as the trail ends at the Connecticut line. The second section we rode, going North from the Brewster trailhead at Lake Tonetta, offers views of the “ice pond” and the “great swamp,” with hills in the distance. Today’s one way mileage for that section was also about 5 miles; a great ride, and you can ride much farther (we often go as far as Whalley Lake, just not today) as the trail goes all the way to Hopewell Junction where you can pick up the Dutchess Rail Trail. Check the Empire State Trail website for more info.
Rode the full trail on Memorial Day and really enjoyed it. It is well maintained; smooth pavement all the way. Mostly good shade and scenic, with lots of woods. A few spots along busy roads, but the trail is well protected throughout; always a sturdy railing between you and the cars. Goes through a few towns for snacks or lunch. Others warned about it being uphill heading north but I found it mostly flat. Some uphill as you approach the Putnam border, but mostly a gentle grade. Never came out of the seat. Overall a great trail.
Rode the full trail on Memorial Day and really enjoyed it. It is well maintained; smooth pavement all the way. Mostly good shade and scenic, with lots of woods. A few spots along busy roads, but the trail is well protected throughout; always a sturdy railing between you and the cars. Goes through a few towns for snacks or lunch. Others warned about it being uphill heading north but I found it mostly flat. Some uphill as you approach the Putnam border, but mostly a gentle grade. Never came out of the seat. Overall a great trail.
I prefer to travel out to Jones in the Fall and Winter months but this trail is great all year round. The board walk gets very crowded on the weekends and throughout the summer, however, the trail continues PAST the board walk (this trail map should be updated!) the concrete trail extends to the west end, there are paths that allow you to check out the fishing spots which require parking permits so being able to get there by bike for free is a plus. Just be aware that after memorial day you must pay $$$ for parking at Jones Beach, which is why I recommend this trail for the off season.
What a lovely trail! We had a great time with our 2 year old daughter on the back of the bike… shaded, not too hilly and playgrounds for her along the way.
I never have been in this place before Is so nice, clean and secure. I would walk again definitely.
I began in Massapequa with the intention of finishing at Woodbury Road. I made it to Trail View Park at mile marker 8 and turned around. Picture perfect biking weather , but first ride of the season. I’ll definitely finish the trail next outing. The trail is well maintained, filled with walkers, joggers and bikers. I’d definitely recommend for walking and biking
The Kennedy Catholic School is private property. Do not enter or depart the trail from the southern endpoint at Kennedy Catholic.
The Kennedy Catholic High School parking lot is private property and they have not given anyone walking the trail permission to access the trail via their parking lot . As with any school they are very protective of the student body and control who has access to the school and parking lot. DO NOT PARK IN THE SCHOOL PARKING LOT. Do not access the trail from the Kennedy Catholic High School.
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