Upcoming 5K Trail Runs within 200 miles of Simsbury, CT on Weekends
Andover, NJ
Hot Chili Challenge
Oct 20, 2024
Westerly, RI
Run for the Pumpkins Trail Race
Oct 5, 2024
Titusville, NJ
Trails4Tails Fest
Oct 19, 2024
Hauppauge, NY
Great Pumpkin Dash Trail 5K
Oct 13, 2024
Stratford, CT
Frosty Forest Trail 5K
Dec 14, 2024
Middleboro, MA
Samuel Fuller School Trail Race
Oct 12, 2024
Fayetteville, NY
Halloween Run
Oct 27, 2024
Harvard, MA
Run for the Hills 5K Trail Race
Oct 27, 2024
Goshen, VT
Goshen Gallop
Jul 12, 2025
Middletown, NJ
Mayor's Challenge 5K
Sep 29, 2024
Waltham, MA
Western Greenway 5K
Oct 27, 2024
Riverhead, NY
Race for the Greenway 5K Trail Run
Oct 27, 2024
Attleboro, MA
Nick's 5K Run
Oct 6, 2024
Hamilton, MA
Thanks for the Trails 5K
Nov 30, 2024
Wareham, MA
Grumpy's Cranberry Harvest 5K
Nov 2, 2024
Woodbury, NY
Rob's Trail Run Edition
Dec 1, 2024
Farmington, CT
Farmington Valley Pumpkin Run
Oct 12, 2024
Dartmouth, MA
DNRT Trail Race
Nov 16, 2024
Kennebunkport, ME
Kennebunkport Conservation Trust Trail Fest
Oct 6, 2024
Wurtsboro, NY
Roosa Gap Roller Coaster Runs
Sep 29, 2024
Cross River, NY
John Jay Community Trail Race
Apr 6, 2025
Wayland, MA
Wayland XC Festival
Oct 13, 2024
Cumberland, RI
F.I.T. TrailFecta
Oct 20, 2024
Nov 28, 2024
Dec 8, 2024
Medford, NJ
Trails Tails and Ales 5K Trail Run
Sep 28, 2024
Oaks, PA
Pumpkin Run 5K
Oct 20, 2024
South Orange, NJ
NJ Trail Series SOMO Winter 1
Nov 16, 2024
NJ Trail Series SOMO Winter 2
Dec 14, 2024
NJ Trail Series SOMO Winter 3
Jan 11, 2025
Keene, NH
Fall Foliage Trail Races
Oct 6, 2024
Warwick, RI
Ocean State 5K Trail Race
Sep 28, 2024
West Orange, NJ
Squatchy Leftovers Trail Race
Nov 30, 2024
Frosty Fat Sass
Jan 25, 2025
Squatchy Surprise
Jul 26, 2025
Milton, VT
GMAA The Hills Are Alive XC 5K
Oct 27, 2024
Wayne, PA
McKaig 5K Trail Race
Oct 6, 2024
Waterville Valley, NH
Fall Foliage Foot Race
Oct 13, 2024
Wilton, CT
Gemstone Sparkle Sprint
Oct 5, 2024
Howell, NJ
Howell 5K Turkey Trot
Nov 17, 2024
Thompson, CT
Thompson Turkey Trot
Nov 10, 2024
Martinsville, NJ
Chimney Rock Trail Race Series 10K & 5K
Oct 5, 2024
Pennington, NJ
Meadows Miler
Nov 2, 2024
Biddeford, ME
Eastern Trail parkrun Biddeford
Jun 7, 2025
Jun 14, 2025
Jun 21, 2025
Jun 28, 2025
48 more
Shirley, MA
Holdenwood Trail Run
Sep 29, 2024
North Grafton, MA
Scaredy Cat K95K
Oct 27, 2024
Harvest Home 5K
Nov 3, 2024
Westminster, MA
One Mission's Conquer the Course
Nov 2, 2024
Glen Mills, PA
Monster Dash 5K at The Bates Motel
Oct 26, 2024
Race for the Watershed: 5K Trail Run & Duck Race
Jun 14, 2025
Malta, NY
Malta 2K, 3K, 5K Trail Race
Oct 20, 2024
Garrison, NY
Castle to River Run
Oct 20, 2024
Chittenango, NY
Clear Path 5K Trail Run
Nov 10, 2024
Meredith, NH
Wanakee Wilderness 5K
Aug 16, 2025
Croghan, NY
AdironDUCK 5K Trail Run
Apr 27, 2025
Gardiner, NY
Gardiner Dump Run
Sep 21, 2025
Pleasant Valley, NY
Billy Goat Trail Run
Oct 20, 2024
Cornwall, CT
Mohawk Mountain Race
Oct 13, 2024
Flourtown, PA
Scouts Bsa Troop 541/542 - Fall Trail Run
Oct 19, 2024
Branchville, NJ
Thunder Chicken Squatch Trail Race
Aug 10, 2025
Willistown, PA
Run-a-Muck with Willistown Conservation Trust
Oct 5, 2024
Meriden, NH
Blackhawk Blaze
Oct 6, 2024
Sat | Sun | Mon | Tue | Wed | Thu | Fri | Multiple |
1. Cutler Park parkrun
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Sep 28, 2024Saturday
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5K trail run
More Information
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Needham, MA
89 miles point to pointNorfolk County, MA
2. Eastern Trail parkrun Biddeford
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Sep 28, 2024Saturday
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5K trail run
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Biddeford, ME
169 miles point to pointYork County, ME
3. Ocean State 5K Trail Race
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Sep 28, 2024Saturday
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5K trail run
More Information
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Warwick, RI
75 miles point to pointKent County, RI
4. Trails Tails and Ales 5K Trail Run
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Sep 28, 2024Saturday
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5K trail run | kids run
More Information
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Medford, NJ
171 miles point to pointBurlington County, NJ
5. Holdenwood Trail Run
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Sep 29, 2024Sunday
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5K, 2K trail run
More Information
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Shirley, MA
79 miles point to pointMiddlesex County, MA
6. Mayor's Challenge 5K
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Sep 29, 2024Sunday
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5K, 1M trail run
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Middletown, NJ
121 miles point to pointMonmouth County, NJ
7. Roosa Gap Roller Coaster Runs
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Sep 29, 2024Sunday
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11.5M, 5K trail run
More Information
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Wurtsboro, NY
90 miles point to pointSullivan County, NY
8. Chasing Ciara's Light 5K/12K Trail Race
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Oct 5, 2024Saturday
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12K, 5K trail run | kids run
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Monroe, CT
41 miles point to pointFairfield County, CT
9. Chimney Rock Trail Race Series 10K & 5K
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Oct 5, 2024Saturday
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10K, 5K trail run
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Martinsville, NJ
126 miles point to pointSomerset County, NJ
10. Cutler Park parkrun
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Oct 5, 2024Saturday
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5K trail run
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Needham, MA
89 miles point to pointNorfolk County, MA
11. Eastern Trail parkrun Biddeford
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Oct 5, 2024Saturday
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5K trail run
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Biddeford, ME
169 miles point to pointYork County, ME
12. Gemstone Sparkle Sprint
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Oct 5, 2024Saturday
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5K trail run
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Wilton, CT
55 miles point to pointFairfield County, CT
13. Run for the Pumpkins Trail Race
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Oct 5, 2024Saturday
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10K, 5K trail run | kids run
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Westerly, RI
62 miles point to pointWashington County, RI
14. Run-a-Muck with Willistown Conservation Trust
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Oct 5, 2024Saturday
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5K trail run
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Willistown, PA
193 miles point to pointChester County, PA
15. Blackhawk Blaze
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Oct 6, 2024Sunday
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1M run | 5K trail run
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Meriden, NH
121 miles point to pointSullivan County, NH
16. Fall Foliage Trail Races
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Oct 6, 2024Sunday
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10K, 5K trail run
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Keene, NH
81 miles point to pointCheshire County, NH
17. Kennebunkport Conservation Trust Trail Fest
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Oct 6, 2024Sunday
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10K, 5K trail run
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Kennebunkport, ME
162 miles point to pointYork County, ME
18. McKaig 5K Trail Race
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Oct 6, 2024Sunday
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5K trail run | kids run
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Wayne, PA
184 miles point to pointDelaware County, PA
19. Nick's 5K Run
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Oct 6, 2024Sunday
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5K trail run
Virtual OptionMore Information
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Attleboro, MA
82 miles point to pointBristol County, MA
20. Norfolk Land Trust Trail Race Series - Haystack Mountain Challenge
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Oct 6, 2024Sunday
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13.1M, 10K, 5K trail run
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Norfolk, CT
22 miles point to pointLitchfield County, CT
For the love of all that Is good And moisture wicking...
Though we Try To be accurate And On top Of things... Race details can change When we aren't lookin. And once in a while we simply make a mistake.
ALWAYS visit the race's website for the most complete and accurate race information.
ALWAYS visit the race's website for the most complete and accurate race information.