Trail Running calendar near Putnam 2026-2027

Enjoy a 3 mile trail run through the scenic Westport Rivers Vineyard & Winery followed by a vineyard celebration with dinner, wine, and live music.

A community 5K trail run, walk and hike in Eisenhower Park Milford on June 7, 2026 supporting the Milford Rotary and the Beth El Center. The course uses a high school cross country route with mostly flat sections and some rolling hills.

Experience a scenic New England trail event in Dunstable with a 5 mile loop or a 6 hour timed challenge. Support the Humane Society while running through historic quarries and former ski hills.

Explore the hill towns of western Massachusetts on a mix of trails and dirt roads. Choose from a 50k, 30k, or 10k distance, with all proceeds supporting the Franklin Land Trust's conservation efforts at the scenic Edge Hill Conservation Are..

Explore the trails of Mansfield Hollow State Park at the Nipmuck South Trail Race. Choose between a scenic 15 mile out and back route or a new, challenging 5K course. Proceeds support local trail stewardship organizations in Connecticut.

Celebrate the longest day of the year with a trail run in Hebron, Connecticut. This event on June 20, 2026, features three distance options on the trails. Choose from a 3 mile, 5 mile, or 8 mile course.

Run a scenic yet rugged half marathon trail race at Lynn Woods Reservation in Massachusetts. This 13.1-mile event features three challenging loops showcasing the historic Stone Tower. The focus is on sustainability and a centralized start/f..

Test your endurance on a 4.25-mile loop in Hamden, CT. Set a goal from a marathon to 50 miles within the 12-hour window. Your registration supports local trail maintenance and comes with unique swag.

Notchview Ultra features a 1.9-mile groomed loop trail in Windsor, Massachusetts. The event includes multiple ultra distances from 6 to 72 hours and a 100.7-mile race. Proceeds support the Trustees of Reservations and a local humane society..

Run the TARC Blue Hills Skyline 12K on June 21 in Milton, MA, tackling about 2,300 feet of climbing on rocky, technical Skyline trails. Stair climbs and panoramic Boston skyline views make this a memorable trail challenge.

The Run For Ryan Memorial Run will take place in Putnam on Saturday 18 July 2026. You can run 5 kilometers.

A unique trail race at Soapstone Mountain featuring six ascents. Runners circle the base and climb each upward trail they find, finishing with the infamous Killer Hill. The challenging course includes rocky and steep terrain.

An evening cross-country event at Stonington High School on August 5, 2026, featuring a 5K and a Children's 1/2 Mile for ages 10 and under. The course starts and finishes on the track and includes campus streets, trails, grass, and a bridge..

Experience the Trail Animals Running Club Summer Classic at Medfield's Noon Hill and Shattuck Reservations, a scenic and challenging 10 mile loop of forested singletrack that climbs to a Noon Hill vista. Distances include 10 miles, 40 miles..

Join an 8-hour celebration run on a 5K trail loop in Tolland, CT. Earn raffle tickets for each loop and enjoy a community potluck. All participants receive a special 50th-anniversary gift.

Experience a scenic off-road trail run or walk through the conservation lands of White Barn Farm. This cup-less 5k event supports local sustainable agriculture and community food security in Wrentham.

Run the Jug End Loop Ultra in the scenic Jug End State Reservation. Choose between a 4.2-mile race or a 6-hour ultramarathon on a challenging loop trail. All finishers receive a handmade ceramic mug, and the event supports local charities.

The annual Vineyard Hill Trail Run features a scenic 5K/10K course over Vineyard Hill and through Bradley Palmer State Park. It's part of the North Shore Trail Series and includes a fully marked trail with an aid station.

Challenge yourself on a 10-mile loop course through the Big River Management Area in Rhode Island. Choose from 100-mile, 12-hour, or 6-hour ultra distances on a relatively flat trail. All participants receive a race sweatshirt, with a speci..

Traverse the scenic ski slopes and forest trails of Wachusett Mountain in this timed event featuring loops from 7 to 28 miles. Earn a finisher medal within 10 hours and enjoy a post trek party at the mountain base.