Trail Running calendar near Upton 2026-2027

The second annual Live Free Fun Run and Festival in Woburn features a scenic 2.5 mile off-road run or walk around Horn Pond. The festival includes food trucks, a DJ, kids activities and tables from over 25 local mental health and substance..

A family friendly Monday night trail series in Nashua offering 5K and 5-mile races plus virtual options, themed evenings with music and giveaways, and occasional frozen treats at the finish.

A weekly 5K cross-country trail series at Worthington Winery in Somers, Connecticut, held Wednesdays from June 3 to July 1, 2026. The course runs through backwoods and vineyard areas with views of ponds and a covered bridge.

Point-to-point trail events of 112 miles and 50 miles along the New England Trail in Connecticut. Self-navigation is required, crew support expected, and donations to the Connecticut Forest and Park Association are required for entry.

A community running event on June 6, 2026 in Holliston with 5K, 10K, and a Kids Fun Run on the flat Holliston Rail Trail. Registration opens March 1; fees are $30 for the 5K and 10K and $5 for the kids run.

A 20 mile single-loop hike through Wompatuck State Park near Boston on June 6, 2026, with aid stations roughly every 5 to 7 miles, finisher medals and certificates. The event is currently sold out.

A group run on the Ocean State Ultra 10 mile loop in West Greenwich, RI. The route allows runners to turn back early and participants must wear orange because it is hunting season.

A trail run at Westport Rivers Vineyard & Winery on June 7, 2026, covering about 3 miles of mixed trails and finishing among the vines. The event includes dinner, wine, music and a souvenir wine glass, with BBQ only options available.

Run for RMC on June 7, 2026 at Stanley Park in Westfield MA offers a 5K trail run and a 1 mile accessible route to raise awareness of renal medullary carcinoma and support related programs.

A ninth annual trail race through Dogtown Common on a rugged 5.4 mile course that mixes carriage roads and technical rock sections. Walkers are welcome, course maps are available, and prizes and event shirts are offered.

A free community trail event in Farmington offering shoe demos and short runs on local trails. Options include about 5 km, 1.7 mile, and 1 mile routes, with snacks and drinks afterwards.

A five mile fun run along the Cheshire Rail Trail from Fitzwilliam Depot to the restored Troy Depot on June 13, 2026. The day features food and festivities, a children's loop, return transport on request, and benefits local historical socie..

Experience a day of trail running and mountain biking at the Norbrook Farm Brewery Trail Festival. Enjoy multiple race distances, local food trucks, and rewards at this scenic Connecticut brewery.

A second annual trail event in Dunstable, Massachusetts offering a 5 mile loop or a six hour race of repeated 5 mile loops. The course follows an old railroad bed, an arched stone bridge, woods, peaks, and single track trails.

A low key trail event in Ashfield, MA on June 13, 2026 that showcases local trails and preserved lands. It offers 50 km, 30 km and 10 km distances and raises funds for the Franklin Land Trust.

A loop based endurance race near Big River Management Area in West Greenwich, RI where runners must complete each circuit within 60 minutes to continue; laps repeat at one hour intervals until only one runner remains.

A mixed-surface 5 km race and one-mile fun run at Hampshire Regional High School in Westhampton on June 13, 2026. The 5 km combines paved roads and wooded trails; awards, refreshments, restrooms and parking are provided.

A community fun run on 06/13/2026 behind Madbury Town Hall with a 1K kids run and a 5K route through Kingman Farm trails. Registration is free and donations for park improvements are accepted on the day.

Trail races in Mansfield Hollow State Park offering a 15.7 mile out-and-back on the Nipmuck Trail and a new in-park 5K, with varied terrain, marked courses, and proceeds benefiting Connecticut trail stewardship groups.

A family-friendly three-loop course of about 5 km through Natick Community Organic Farm with mixed trail, field and road surfaces. All participants receive a chicken medal and proceeds support the farm’s education and teen programs.