Where the Pavement Ends
2025-09-14 07:30 - 09:00 (America/New_York) | Ridgebury School, Ridgefield, CT, 112 Bennetts Farm Rd, Ridgefield, CT, 06877, United States
On Sunday, September 14, 7:30 a.m., run Where the Pavement Ends, a fun and challenging 4-plus miles of sometimes narrow, sometimes hilly, always beautiful trails. It is a great mix of fire road, single track, flats, hills, and one fast downhill section right towards the end. Park at the Ridgebury School, Ridgefield, CT and walk over the Serfilippi Field, ready to run at 7:30 a.m. or register for the Double starting at 7:00. Cobweb Crew starts at Lewisboro Town Park at 5:00 a.m. but will return in time to make it to the race. If you’re not looking to race and want to stay closer to home, I’d suggest meet at 8:00 in Lewisboro Town Park and run the Town Park to Green loop. But bring your own maps, I’ll be at Where the Pavement Ends.
No Rookie Runners run this week but this race is rookie-friendly.

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Trail Tuesday
2025-09-16 05:30 - 07:00, 2025-09-23 05:30 - 07:00, 2025-09-30 05:30 - 07:00, 2025-10-07 05:30 - 07:00, 2025-10-14 05:30 - 07:00, 2025-10-21 05:30 - 07:00 | Ward Pound Ridge Reservation, Michigan Road Lot, Michigan Road, Pound Ridge, NY, 10576, United States
Looking for a mid-week run? Meet at Ward Pound Ridge Reservation, Michigan Road Lot, on Tuesdays at 5:30 a.m. for a run finishing up between 7:00 and 7:30. It’s a great way to get your run in early.

Workout Wednesday—Kimberly Bridge
2025-09-17 05:30 - 07:00, 2025-09-24 05:30 - 07:00, 2025-10-01 05:30 - 07:00, 2025-10-08 05:30 - 07:00, 2025-10-15 05:30 - 07:00, 2025-10-22 05:30 - 07:00 | Ward Pound Ridge Reservation, Kimberly Bridge, Reservation Road, Pound Ridge, NY, 10576, United States
Are you looking to amp up your running? Add hill repeats and speed work on Wednesdays at 5:30 a.m. This week, meet at Ward Pound Ridge Reservation, Kimberly Bridge Lot, at 5:30 a.m., for 90 minutes of Hill Repeats. At a 13% average incline, the Blue Hill segment is one of the steepest in the Rez and the perfect training ground for any upcoming race. The .6 mile uphill contains just over 400 feet of vertical gain while the downhill is a great quad-shredding exercise. If you need to train with poles, this is a good course to do so. We’ll aim for 4 or 5 repeats and see what we have left after that.

Trail Thursday
2025-09-18 05:30 - 07:00, 2025-09-25 05:30 - 07:00, 2025-10-02 05:30 - 07:00, 2025-10-09 05:30 - 07:00, 2025-10-16 05:30 - 07:00 | Ward Pound Ridge Reservation, Michigan Road Lot, Michigan Road, Pound Ridge, NY, 10576, United States
Looking for a mid-week run? Meet at Ward Pound Ridge Reservation, Michigan Road Lot, on Thursdays at 5:30 a.m. for a run finishing up at 7:00.

All These Miles—The Exhibition
2025-09-18 17:30 - 19:00 | Bedford Playhouse, 633 Old Post Rd, Bedford, 10506, United States
On Thursday, September 18, at 5:30 p.m., meet at Bedford Playhouse for the opening of my first solo show of All These Miles. Many of you know that since January 1, 2023, I’ve been creating art based on every run I’ve done using photographs and data from the run. Since the start of the project, I’ve completed over 700 runs and traveled over 6,000 miles. A dozen pieces are installed in the café area of Bedford Playhouse until late August but come out for the opening on the 18th. If you can’t make the opening, stop by any time and see the work for yourself. More pieces are available at leewillett.art/all-these-miles.

Alan's Adventure
2025-09-20 07:00 - 09:00 | Ward Pound Ridge Reservation, Michigan Road Lot, Michigan Road, Pound Ridge, NY, 10576, United States
On Saturday, September 20, at 7:00 a.m., meet at Ward Pound Ridge Reservation, Michigan Road Lot, ready to run a course based on local events—a hiker lost in the Rez in 2024. This twisted course takes us down the Rock Trail, past Raven Rocks, and back via the Yellow trail. Shorter options are available as well. Early Risers start at 6:00 for a few more miles before.

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Last time we ran this course was September 21, 2024

Michigan to Kimberly V3
2025-09-21 08:00 - 09:30 | Ward Pound Ridge Reservation, Michigan Road Lot, Michigan Road, Pound Ridge, NY, 10576, United States
On Sunday, September 21, at 8:00 a.m., meet at Ward Pound Ridge Reservation, Michigan Road Lot, ready to run the Michigan to Kimberly v3 loop. This version of the classic course offers distances from 5 to 7.5 miles but you can visit the Overlook as well to add even more. Cobweb Crew starts at 5:00; Early Risers at 7:00 a.m.
Rookie Runners start at 7:00 a.m. for a shorter distance and easier pace if necessary.
Walkers/Hikers start at 8:00 on a short course of around 4 miles.

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The last time we ran this course was April 13, 2025

Kimberly to Blue Route
2025-09-27 07:00 - 09:00 | Ward Pound Ridge Reservation, Kimberly Bridge, Reservation Road, Pound Ridge, NY, 10576, United States
Kimberly Bridge
On Saturday, September 27, at 7:00 a.m., meet at Ward Pound Ridge Reservation Kimberly Bridge Lot ready to run the Kimberly to Blue Route. Start down the Blue trail and choose from 5 miles, 6.5 miles, or 8 miles. Early Risers start at 6:00 for a few extra miles.

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Last time we ran this course was September 28, 2024

Trailside to Town Park
2025-09-28 08:00 - 10:30 | Trailside Museum, Reservation Road, Pound Ridge, NY, 10576, United States
On Sunday, September 28, at 8:00 a.m., meet at Ward Pound Ridge Reservation, Trailside Museum Lot, ready to run the Trailside to Town Park loop. This course loops around the northern part of the Rez, up the Howland Drive segment, before taking four different options for returning to the lot. An optional excursion into Lewisboro Town Park for the longer distances will add a half mile or so. Cobweb Crew starts at 5:00; Early Risers start at 7:00.
Rookie Runners arrive at 7:00 a.m. for a shorter loop at an easier pace.
Walkers/Hikers start at 8:00 on a short course of around 4 miles.

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The last time we ran this course was May 24, 2025

Trail Running Film Festival
2025-10-02 19:00 - 20:30 | Prospector Theater, 25 Prospect Street, Ridgefield, 06877, United States
On Thursday, October 2, at 7:00 p.m., join the Ct. Run Co. at the Trail Running Film Festival at the Prospector Theater in Ridgefield. This one-night-only event brings to life great tales from the running community but you don’t need to be a trail runner to enjoy an evening of fun and camaraderie. Sponsored by CT Run Co. and Brooks. 100% of ticket sales benefit the Prospector Theater. This is the same film festival we had at the Bedford Playhouse in the spring so this is your chance to relive the event or see it if you weren’t able to attend.
Tickets and details ››

TRFF 2025 Global Tour Trailer ››.

Westmoreland Perimeter Loop
2025-10-04 07:00 - 09:00 | Westmoreland Sanctuary, 260 Chestnut Ridge Rd, Mt. Kisco, NY, 10549, United States
On Saturday, October 4, at 7:00 a.m., meet at Westmoreland Sanctuary on Chestnut Ridge Road in Mount Kisco when we run the 6 mile perimeter loop including the newest acquisition—the Raptor Ridge trail. Early Risers can meet at Butler Sanctuary just across the street at 6:00 a.m. for a 4-mile loop first. See the map ››. Then, after the run, head over to Mimi’s Coffee House in Mt. Kisco for a cup of coffee, tea, or whatever.

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Last time we ran here was July 5, 2025

Five Bridges Run
2025-10-05 08:00 - 09:30 | Lewisboro Town Park, Upper Lot, 1091 Old Post Road, Cross River, NY, 10590, United States
On Sunday, October 5, at 8:00 a.m., meet at Lewisboro Town Park (upper lot until full, then lower lot) ready to run the Five Bridges run. The 7.5 mile version of the run passes by five of the major bridges in the Rez but you have options for longer and shorter distances should you choose. Cobweb Crew starts at 5:00; Early Risers at 7:00.
Rookie Runners start at 7:00 for a shorter distance and easier pace.
Walkers/Hikers start at 8:00 on a short course of around 4 miles.

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Last time we ran this course: March 16, 2025

Meadow to Armstrong
2025-10-11 07:00 - 09:00 | Ward Pound Ridge Reservation, Meadow Lot, Reservation Road, Pound Ridge, NY, 10576, United States
On Saturday, October 11, at 7:00 a.m., meet at Ward Pound Ridge Reservation, Meadow Lot, ready to run the Meadow to Armstrong Loop. This course offers distances of 5, 7, and 8.5 miles and takes us off the reservation into two small preserves to the west of the park. The out-and-back nature of this gives you plenty of choices to customize distance including returning through the BRLA trail off Honey Hollow Road. Early Risers start at 6:00.

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Last time we ran this was June 1, 2025

Gerrython
2025-10-12 08:00 - 10:00 | Ward Pound Ridge Reservation, Michigan Road Lot, Michigan Road, Pound Ridge, NY, 10576, United States
On Sunday, October 12, at 8:00 a.m., meet at Ward Pound Ridge Reservation, Michigan Road Lot, ready to run the Gerrython. You have options for 13, 10, 7, and 5 mile loops. Note that the bridge is out over the stream behind the park office so the 7 and 13 milers can follow FH to intersection 1 and the 10 and 5 milers can follow the road to Schoolhouse. Cobweb Crew starts at 5:00; Early Risers at 7:00.
Rookie Runners start at 7:00 for a shorter distance and easier pace.
Walkers/Hikers start at 8:00 on a short course of around 4 miles.

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From the archives: The last time we ran this course was October 20, 2025.

Michigan to Dancing Rock
2025-10-18 07:00 - 09:00 | Ward Pound Ridge Reservation, Michigan Road Lot, Michigan Road, Pound Ridge, NY, 10576, United States
On Saturday, October 18, at 7:00 a.m., meet at Ward Pound Ridge Reservation, Michigan Road Lot, ready to run the Michigan to Dancing Rock course. This loop starts with a climb to the Overlook then follows some of the lesser-used trails in the park. Options include 4.5, 6.6, 8 and 9 mile loops. Early Risers start at 6:00 for a few extra miles.

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Last time we ran this course was June 28, 2025

Run the Farm
2025-10-19 09:30 - 11:00 | Muscoot Farm, 51 NY-100, Katonah, NY, 10536, United States
This Sunday, October 19, at 9:30 a.m, meet at Muscoot Farm (http://goo.gl/maps/dTDiT) for the Run the Farm 5 Mile Trail Race. This 5 mile course starts from the farm and follows the outlying trails around Muscoot. You can download a map of the five-mile course here.
8:30 a.m. Kids’ Race (7 to 12-year-olds)
8:45 a.m. Kids’ Race 2 (6 and under)
9:30 a.m. 5 Mile Race
Cobweb Crew starts at 5:00 a.m. from Ward Pound Ridge Reservation, Meadow Lot, for a few miles before the race.
For more information, visit RunTheFarm.org.

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