Guilford
Trail Running Calendar near Guilford 2026-2027
Explore the top trail runs near Guilford for 2026-2027! We've gathered 22 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
August 2026
A 2.5 mile trail run and walk at Wildwood State Park on August 8, 2026, held rain or shine. Registration fees and a donation option are listed, and personalized bibs are available for those who register three weeks in advance.
Experience a community trail run through Elm Ridge Park benefiting the Rocky Hill Fire Department and Library. This event features a two loop trail course for adults and a fun medal race for kids.
September 2026
Experience a scenic 3.3 mile trail run or hike through the Oswegatchie Hills Nature Preserve. Support local land conservation while enjoying a timed course around Clark Pond followed by an awards ceremony with refreshments.
An obstacle-based 5K at Short Beach, Stratford on September 12, 2026, with 18+ obstacles and fundraising for the Sterling Community Center.
October 2026
A 30-hour trail ultra at Roosevelt Forest in Stratford CT with 2.5-mile loops, buckles at 100 miles, and a 50 participant field limit.
Run through 300 acres of scenic vineyards on a flat trail course in Peconic. Enjoy live music, food trucks, and a post-race glass of wine at this chip-timed autumn event.
Multi-day trail event in Rocky Point, NY on a 10.48 mile loop repeated for distances up to 150 miles, with two stocked aid stations and crew support.
A 3.5 mile trail run and walk on the scenic, flat Mill Pond Trail at Woodtick Recreation in Wolcott CT on October 17, 2026. Tiered online registration is available and a post-event meal is included with registration.
An off‑road 50K around Guilford, CT on rocky single track and rolling forest roads, with aid station cutoffs and recommended marathon-level experience.
A community run at Ives Farm hosted by Cheshire Community YMCA and Cheshire Land Trust. Features a trail 5K, a youth Y Cup relay with elementary teams, a free Pumpkin Dash for young children and family fall activities.
A 5K Run / Walk and Kids Fun Run at Hallock State Park on October 25, 2026, with a virtual 5K option. Proceeds support the Long Island Greenway and include a post-race wine crawl with vendor specials for participants 21 and over.
November 2026
Trail races at YMCA Camp Sloper on November 21, 2026 offering a 400 minute loop event and a 4 mile race with chip timing and on-course aid.
December 2026
A repeated 3.3 mile out and back on the Tower Trail at Sleeping Giant State Park, with four hour and eight hour options and a cupless aid station at start and finish.
March 2027
Chip timed 5k run and walk at Osprey’s Dominion Vineyards in Peconic, NY on March 20, 2027, over a two lap cross country loop with a postrace wine pour for eligible participants. Registration includes a T shirt, collapsible wine glass and finisher me..
April 2027