When I moved to New York City, I figured my trail running days would be limited.
Fortunately, I was wrong. While every run in the urban jungle of the Big Apple offers unique, adventurous elements, there are plenty of places to run on dirt in and around the city. And within about 90 minutes of New York City, runners can find a surprisingly diverse mix of trail races—from technical mountain-style events in the Hudson Highlands to looped endurance races on Long Island and true wilderness ultras just slightly farther north.
The terrain ranges from rocky, rooty singletrack with steep climbs to smooth, runnable dirt trails, offering options for every skill level. Many of these races feature significant elevation gain, dense forests, and scenic ridgelines, giving a true trail experience close to a major urban center.
Here is a rundown of some of the best trail races within about 75 miles of New York City this summer and fall.
In addition to the events highlighted below, also check out the Mine Hill Half Marathon (May 24, Roxbury, Connecticut), MCW The Tatum Classic (May 31, Middletown Township, N.J.), Ansonia Six Hour Trail Run (June 13, Ansonia, Connecticut), Brooksvale 12-Hour (June 27, Hamden, Connecticut), Centurion Ultra Trail Event (June 27, Stratford, Connecticut), The Revolution (July 11, Redding, Connecticut), The Squatchy Surprise (July 25, Millburn, N.J.), Tappen Brook 5K (Aug. 9, Bridgewater, Connecticut), Fall Back into the Trails Series (Oct. 31, Lagrangeville, N.Y.), 8 Hours at the Farm (Nov. 1, Brookfield, Connecticut), Storybrook Half Marathon (Nov. 21, Stratford, Connecticut), Egg Nog Slog (Dec. 6, West Orange, N.J.), MCW The Holmdel Classic (Dec. 12, Holmdel, N.J.)
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Cayuga Trails
May 30, Ithaca, New York
50 miles, 50K
Cayuga Trails is a scenic and challenging race known for its gorges and waterfalls. The course is about 95 percent singletrack with significant elevation gain (up to ~10,000 feet in the 50-miler). Runners traverse stone staircases, forest trails, and technical terrain. The combination of waterfalls and rugged trails makes it one of the most scenic races in the Northeast.
Information and registration: Cayuga Trails
Sri Chinmoy 24- and 12-Hour Races
June 13-14, Congers, New York
24-Hour, 12-Hour, 26.2 miles, 13.1 miles
The Sri Chinmoy 24-Hour, 12-Hour, Midnight Marathon, and Sunset Half-Marathon are held on a scenic and fast 2.95-mile pancake flat paved loop at Rockland Lake State Park. The races attract everyone from first-time ultrarunners to elite multiday athletes chasing national and world records, and they are widely respected in the ultrarunning world for their welcoming atmosphere, precise organization, and deep connection to the history of multiday endurance running. Whether you’re attempting your first ultramarathon or chasing a national record, the event strives to provide a high level of runner support and service for athletes of all experience levels.
Information and registration: Sri Chinmoy 24- and 12-Hour Races
XTERRA Transcend Trail Run
June 20, Randolph, New Jersey
13.1 miles, 10K, 5K
The XTERRA Transcend Trail Run is a scenic trail running event held June 20 at Dickerson Mine Preserve in Randolph, featuring 5K, 10K, and half marathon distances on fast, flowing singletrack trails. The courses wind through shaded forests and lakeside terrain with moderate elevation gain, making the race one of the more approachable and beginner-friendly events in the XTERRA trail running series.
Known for its welcoming atmosphere and smooth, runnable trails, the event blends scenic woodland running with a festive post-race gathering at the lakeside Black River Barn. The half marathon also serves as a qualifier for the XTERRA Trail Run World Championship, attracting both competitive runners and newer trail athletes seeking a fun and accessible race experience.
Information and registration: XTERRA Transcend Trail Run
Ruck Around The Race Weighted Race
June 20, Valley Cottage, New York
8 Hours
The Ruck Around the Lake Weighted Race is a unique endurance event at Rockland Lake State Park near Valley Cottage. Instead of a traditional running race, participants carry weighted packs, sandbags, or weight vests while completing repeated 3-mile loops around Rockland Lake during an 8-hour challenge.
The event uses a “pound-mile” scoring system that multiplies the weight carried by the distance completed, allowing competitors to strategically adjust their loads between laps. Known for its military-inspired rucking culture, the race blends endurance, strength, and mental toughness in a format that appeals to ultrarunners, hybrid athletes, and tactical fitness enthusiasts.
Information and registration: Ruck Around The Race Weighted Race
Wakely Dam Ultra
July 18, Piseco, New York
55K
The Wakely Dam Ultra is a rugged backcountry trail running event held in the remote Adirondack forests near Wakely Dam. The race sends runners on the Northville-Placid Trail through the Moose River Plains Wild Forest on a mix of forest roads, technical singletrack, muddy sections, and rolling wilderness terrain surrounded by dense pine forests, wetlands, and isolated backcountry scenery.
Known for its grassroots atmosphere and remote setting, the Wakely Dam Ultra offers a true wilderness ultrarunning experience with sparse aid, limited cell service, long stretches of solitude, and 3,300 feet of elevation gain. The race emphasizes self-reliance and backcountry navigation as runners traverse rugged wilderness trails with no road crossings and about 3,300 feet of vertical gain.
Information and registration: Wakely Dam Ultra
Red Wing Trail Challenge
July 5, Lagrangeville, New York
60K, 30K, 15K
Located in the Hudson Valley, the Red Wing Trail Challenge features looped courses with significant elevation gain. The terrain includes technical singletrack, rocky sections, and sustained climbs that accumulate quickly. The 60K includes roughly 6,600 feet of climbing, making it a demanding mid-summer race. Runners experience dense forest, ridgelines, and classic East Coast trail conditions.
Information and registration: Red Wing Trail Challenge
Trail Night NJ
July 8, West Orange, New Jersey
5K, Kid’s Race
Trail Night NJ is a community-focused Wednesday evening trail running event held at South Mountain Reservation in New Jersey, featuring a fast and approachable 5K course on scenic local trails. Designed for runners of all levels, the event offers a relaxed but energetic atmosphere where participants can race hard, enjoy a casual midweek run, or simply connect with the local trail running community. The event centers around a lively start-finish festival area with a DJ, vendors, and food trucks, creating a social post-run gathering that blends trail running with community and outdoor culture.
Information and registration: Trail Night NJ
MCW Westfield Ultra
Aug. 1, Westfield, New Jersey
24 hours, 12 hours, 9 hours, 6 hours, 3 hours
The MCW Westfield Ultra is a timed endurance running event held at Tamaques Park in Westfield, featuring 3-, 6-, 9-, 12-, and 24-hour race formats on a flat 0.8-mile loop course. Runners complete as many laps as possible on paved and gravel paths, with the flexible format and strong support making the event appealing to both first-time ultrarunners and experienced athletes chasing high mileage goals. Organized by MissionCleanWater, the event also raises funds for clean water and sanitation projects in underserved communities.
Information and registration: MCW Westfiled Ultra
Ridge Reaper Trail Runs
Aug. 1, Cross River, New York
50 miles, 50K, 25K
Held in Ward Pound Ridge Reservation about an hour from NYC, this new race features rugged trails and steep climbs. The course is known for technical footing, including rocks, roots, and twisting singletrack. Elevation gain is significant, especially for the longer distances. The race delivers a challenging and technical trail experience in Westchester County.
Information and registration: Ridge Reaper Trail Runs
Thunder Chicken Squatch Trail Jamboree
Aug. 9, Branchville, New Jersey
17 miles, 10K, 10K Ruck, 5K
The Thunder Chicken Squatch Trail Jamboree is a quirky, community-driven trail running event held in Stokes State Forest, featuring a mix of rugged trail races and endurance challenges on the rocky, technical terrain of northwestern New Jersey. Set among forested singletrack, rolling hills, stream crossings, and root-filled trails, the event combines demanding East Coast mountain running with a fun-loving “Squatch”-themed festival atmosphere. Known for its grassroots spirit, lively aid stations, and offbeat trail culture, the Thunder Chicken Squatch Trail Jamboree emphasizes camaraderie and adventure as much as competition.
Information and registration: Thunder Chicken Squatch Trail Jamboree
Fabulous Fahnestock Trail Races
Aug. 15, Cold Spring, New York
50K, 25K, 5.5 miles
Held in Fahnestock State Park, this race offers a mix of approachable and technical terrain within a scenic Hudson Valley setting. The course blends smooth dirt roads, flowing singletrack, and more technical trail sections, with steady climbs and descents throughout. Runners pass lakes, ponds, and wooded terrain, creating a varied and engaging course profile. With multiple distances and generous support, it’s both beginner-friendly and rewarding for experienced trail runners.
Information and registration: Fabulous Fahnestock Trail Races
Dirty Dozen 50K
Aug. 29, New York, New York
50K
The Dirty Dozen 50K is a difficult urban trail race in Forest Park in Queens, challenging runners to tackle repeated climbs on some of the city’s toughest hills and staircases. Inspired by Pittsburgh’s famous Dirty Dozen cycling challenge, the course features a 2.5-mile counterclockwise loop along the scenic Orange Trail, repeated 12 times for the full distance. Though modest on paper, each lap includes roughly 300 feet of elevation gain, creating a surprisingly demanding cumulative climb over the course of the race. Known for its unconventional format, the Dirty Dozen 50K blends urban adventure with trail running culture, forcing runners to repeatedly grind up steep ascents while navigating parks, paved paths, dirt trails, and staircases.
Information and registration: Dirty Dozen 50K
Kingwood Ultras
Sept. 11-13, Frenchtown, New Jersey
100 miles, 48 hours, 24 hours, 50 miles, 12 hours, 26.2 miles, 6 hours, 10K
The Kingwood Ultras are grassroots trail running events held each summer in the scenic countryside of New Jersey, featuring ultra-distance races on rolling rural trails, forest paths, and quiet backroads throughout the Kingwood Township area. The courses combine runnable terrain with steady hills, shaded woodland sections, creek crossings, and pastoral farmland scenery along the Delaware River region. Known for their relaxed community atmosphere and welcoming trail culture, the Kingwood Ultras attract both experienced ultrarunners and first-time endurance athletes.
Information and registration: Kingwood Ultras
Boulder Field 100
Sept. 12, Jim Thorpe, Pennsylvania
100K, 50K, 18 miles
The Boulder Field 100 is a rugged mountain ultramarathon in northeastern Pennsylvania, featuring steep climbs, rocky singletrack, punishing descents, and notoriously technical boulder fields throughout the Pocono Mountains. Known as one of the Northeast’s toughest trail races, the event challenges runners with remote wilderness terrain, relentless elevation changes, and demanding East Coast mountain trails. Despite its difficulty, the race rewards runners with scenic forest landscapes, rugged backcountry terrain, and a true old-school ultrarunning atmosphere.
Information and registration: Boulder Field 100
Shawangunk Ridge Trail Run
Sept. 12, New Paltz/Rosendale, New York
70 miles, 30 miles, 13.1 miles
The Shawangunk Ridge Trail is known by locals as the SRT, which is a favorite for long weekend runs and this race weekend. The race is run on a point-to-point course that traverses the rugged Shawangunk Ridge, which is known for its dramatic cliffs and exposed ridgelines. The course includes technical singletrack, carriage roads, and rocky terrain with sustained elevation gain. Distances range from a challenging half marathon to a demanding 70-mile ultra. The combination of technical footing and expansive ridge-top views makes it a classic Northeast trail event.
Information and registration: Shawangunk Ridge Trail Run
Wild Goose Trail Festival
Sept. 19-20, Hewitt, New Jersey
100 miles, 100K, 50 miles, 50K, 30K, 13.1 miles, 10K, 1 mile kids race
The Wild Goose Trail Festival is a community-focused trail running weekend held at Wawayanda State Park in Hewitt. The festival combines rugged trail racing with scenic forest terrain, lively aid stations, generous cutoffs, and a welcoming grassroots atmosphere designed for both first-time ultrarunners and experienced endurance athletes. (The 100-mile race includes a 36-hour cutoff, making it especially appealing for runners pursuing their first buckle.)
Beyond the races, the festival includes trail running panels, a film screening, free camping for participants and crews, and a full weekend of community-driven events that celebrate trail running culture. Known for its supportive environment, beautiful trails, and “squatch”-inspired vibe, the Wild Goose has become a unique East Coast trail running gathering that blends endurance racing with festival energy. (The event supports its non-profit partner, Bigger Than The Trail.)
Information and registration: Wild Goose Trail Festival
Brookfield Classic
Sept. 19, Brookfield, New York
50K
Just over the New York/Connecticut border, this race offers a classic New England trail experience within the wooded terrain of the Charles E. Baker State Forest. The course features rolling terrain with a mix of dirt trails and technical sections. Elevation gain is moderate but consistent throughout.
Information and registration: Brookfield Classic
Hook Mountain Ultra
Sept. 19, Upper Nyack, New York
50 miles
Set in Harriman State Park, this race features rugged trails with steep climbs and technical terrain. The course includes rocky singletrack, exposed ridgelines, and sustained elevation gain. The 50-mile distance demands both endurance and technical skill. Scenic overlooks of the Hudson River add to the experience.
Information and registration: Hook Mountain Ultra
Pawling 24-Hour Trail Festival
Sept. 19, Pawling, New York
6 hours, 12 hours, 24 hours
This timed endurance event takes place on looped trail courses in the Hudson Valley. The terrain is mostly runnable dirt trails with moderate elevation gain. Runners can choose from multiple timed formats, testing endurance and pacing strategy. The event blends community atmosphere with flexible race formats.
Information and registration: Pawling 24 Hour Trail Festival
Cat’s Tail Trail Marathon
Sept. 26, Shandaken, New York
26.2 miles
The Cat’s Tail Trail Marathon is a rugged mountain race held in the Catskill Mountains near Shandaken. The point-to-point 26-mile course crosses the Slide Mountain Wilderness Area with nearly 7,000 feet of elevation gain, taking runners over steep ridgelines, rocky technical trails, and iconic Catskills peaks including Slide, Cornell, Wittenberg, and Panther Mountains.
Known for its punishing climbs, technical descents, and classic East Coast mountain terrain, the Cat’s Tail has become one of the Northeast’s premier trail marathons. The race blends rugged wilderness scenery, strict qualifying standards, and a grassroots mountain-running atmosphere that attracts experienced trail runners looking for a true Catskills challenge.
Information and registration: Cat’s Tail Trail Marathon
Water Gap 50K and Half
Sept. 26, Milford, Pennsylvania
50K, 25K
The Water Gap 50K and Half is a scenic trail running event held each fall in the Delaware Water Gap region along the border of New Jersey and Pennsylvania. The race follows the rolling McDade Trail through the Delaware Water Gap National Recreation Area, offering runners a fast and runnable mix of cinder path, smooth singletrack, forested trail, and riverside scenery framed by steep Appalachian ridgelines. Known for its relatively non-technical terrain and beautiful river views, the event appeals to both experienced ultrarunners chasing fast times and newcomers attempting their first ultra.
Information and registration: Water Gap 50K and Half
Tesla Hertz Run
Oct. 10, Rocky Point, New York
100 miles, 100K, 50 miles, 50K
Taking place in the Rocky Point pine barrens on Long Island, this race features a flat but demanding 10.48-mile looped course through forested trail systems. The terrain is 99.8 percent trail—mostly smooth dirt singletrack—making it highly runnable but mentally challenging due to repetition. Distances range from 50K to 100 miles, attracting a wide range of runners. The race emphasizes endurance and pacing over technical difficulty.
Information and registration: Tesla Hertz Run
Big Bear Squatch South
Oct. 18, Tuxedo, New York
13.1 miles, 10K
The Big Bear Squatch South is a rugged trail running event held in the mountains surrounding Tuxedo, featuring challenging distances that traverse the rocky, technical terrain of Harriman State Park. The race sends runners across steep climbs, root-filled singletrack, exposed rock slabs, forested ridgelines, and rolling East Coast mountain trails that are known for being deceptively difficult despite relatively modest elevation profiles.
Known for its grassroots atmosphere and “squatch”-themed adventure vibe, the event blends tough mountain running with a fun, community-driven trail culture. The courses highlight the rugged beauty of the Hudson Valley region while delivering a technical and physically demanding trail running experience that appeals to both newer ultrarunners and experienced East Coast mountain athletes.
Information and registration: Big Bear Squatch South
WXT Ultra
Oct. 24, Titusville, New Jersey
50K, 25K
The WXT Ultra is a trail running event held at Washington Crossing State Park, featuring 25K and 50K races on the historic trails of central New Jersey. The courses traverse technical singletrack, forest trails, rocky sections, creek crossings, and rolling terrain through Washington Crossing Park, Baldpate Mountain, and the challenging Rock Hopper trail system.
Known for its scenic terrain and grassroots atmosphere, the WXT Ultra blends demanding East Coast trail running with Revolutionary War history, as parts of the route follow trails once used by George Washington’s troops. With punchy climbs, rugged rock gardens, and strong aid support, the race offers a challenging but approachable ultramarathon experience.
Information and registration: WXT Ultra
Fall Back Into the Trails
Oct. 31-Nov. 1, Lagrangeville, New York
50K, 100K
Held in the Hudson Valley, this race features looped courses through forested terrain with rolling hills. Trails include dirt singletrack with moderate technical features like roots and rocks. Elevation gain accumulates steadily over the longer distances. The late-season timing adds crisp fall foliage and cooler conditions.
Information and registration: Fall Back Into the Trails
NYC Trail Mix
Nov. 14, Staten Island, New York
50M, 50K, Half Marathon
NYC Trail Mix takes place entirely within Staten Island’s Greenbelt, making it one of the only true trail ultras inside New York City limits. The course uses looped formats through parks like High Rock and La Tourette, featuring rolling terrain and forested singletrack. Trails are mostly dirt with roots and moderate technical sections, creating a runnable but engaging surface. The race offers a surprisingly immersive trail experience in an urban setting.
Information and registration: NYC Trail Mix
Tarrywile Half Marathon
Nov. 15, Danbury, Connecticut
26.2 miles, 13.1 miles, 10K
The Tarrywile Half Marathon is a rugged late-season trail running event with three race distances at Tarrywile Park. The courses wind through the park’s scenic network of forested singletrack, carriage roads, rocky climbs, stream crossings, and rolling hills, giving runners a classic New England trail running experience filled with roots, rocks, mud, and steep punchy ascents.
Information and registration: Tarrywile Half Marathon
PPTC Endurance Fest
Dec. 6, New York, New York
50 miles, 50K
The PPTC Endurance Fest is a winter ultrarunning event held in Brooklyn’s iconic Prospect Park, featuring 50K and 50-mile races on a looped course of rolling park roads and pathways. Organized by the Prospect Park Track Club, the event celebrates New York City’s rich ultrarunning history while offering runners repeated 3.33-mile loops with steady hills, dependable aid stations, supportive volunteers, generous cutoff times, finisher buckles, and a festive community atmosphere that welcomes both first-time ultrarunners and experienced endurance athletes.
Information and registration: PPTC Endurance Fest
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