New Canaan Running Events for Fall 2026: Race Guide

New Canaan has three timed running events in the six weeks between November 7 and December 19. Each one has made a deliberate decision about the ground under its runners' feet. One race moved onto a track to get away from pavement. One is going back to its original course through Waveny Park. One will run its Waveny loop in the opposite direction for the second year in a row so the steepest stretch becomes a downhill.

Those choices line up with the rest of the town's endurance news this fall. A Waveny trail redesign is waiting on town budget approval. Two roads are partway through paving work. And a new shop on Main Street has decided what it won't sell. Here is the season, in order.

The newest race skips the pavement entirely

The season opens with a race that is new this year. The inaugural Ram Council Foundation CD Fun Run takes place Saturday, November 7, at the New Canaan High School Track. The organizers describe the venue as "a safe surface with no asphalt, concrete, or potholes." The format is unusual too. There's no fixed distance. Runners and walkers cover as many laps as they can in 14 minutes and 48 seconds, a time that equals the circumference of a compact disc measured in inches. Runners and walkers get separate lanes, and awards go to the men and women who cover the most distance.

On a track, a timed race measures everyone on the same flat surface no matter their pace, which suits a first-year event that wants every generation out there. The women's race goes off at 9:00 a.m. and costs $48.70 with fees, or $38.10 for ages 9 to 22. The kids' run starts at 9:30 a.m. for $6.30 with fees, and the men's race follows at 9:45 a.m. Registration for the women's race closes at 8:45 that morning. Proceeds support the Ram Council Foundation, which offers New Canaan students in grades 7 through 12 substance-free activities, leadership opportunities, and community engagement.

Waveny twice, in two directions

The next two races both run through Waveny Park, and both made course decisions this year.

The New Canaan Turkey Trot is a 5K on Sunday, November 22, the Sunday before Thanksgiving. It starts at 11:30 a.m. and finishes at the Main House, with ChronoTrack B-Tag timing. All proceeds benefit Open Doors Shelter in Norwalk. The race's registration page sums up this year's change in four words: "Back to the original course." The listed price is $44.30, including a $4.30 fee, with a higher tier of $49.64 shown. Registering before the price goes up after November 5 saves about five dollars.

Four weeks later, the 13th annual New Canaan Santa Run starts and finishes at the park's historic "Castle." It has a 5K and a one-mile walk at 9:30 a.m. on December 19, plus a free children's dash at 9:15 a.m. The organizers are running the 5K in the opposite direction again "which worked out great last year," so one section of the course is now an easy downhill rather than an uphill.

A mid-December race on park trails also has to plan for weather. The Santa Run warns that its courses may change with trail conditions. If traction is a problem, organizers will switch to an alternate road and driveway course, though they note they have never had to. If weather closes the park or the town, the race won't be postponed and entries won't be refunded. Online entry for the 5K and walk is $33.63 with fees. The proceeds support a Feed My Starving Children meal-packing event aiming for 100,000 meals.

Where the training miles fit between race days

Two of the three races finish at Waveny, so training on the race ground is mostly a matter of choosing a loop. The park is open daily during daylight hours and has 3.5 miles of woodland trails across 130 acres. The named options:

• Waveny Perimeter Trail. 1.8 miles around the park, according to the Conservancy's official map.
• Waveny Meadow and Pond Trail. A 1.0-mile loop on the same map.
• New Canaan Land Trust GreenLink. Up to 2.5 miles of trail connecting Irwin Park and the New Canaan Nature Center. It's open dawn to dusk and maintained for pedestrians, and the Land Trust describes its wetlands and woodland loop as a place joggers use.
• Merritt Parkway Trail. Waveny's southernmost trail, about 0.75 miles from the Lapham Road overpass to the southbound Exit 14 ramps.

As fall moves toward winter, daylight hours set the schedule. Both Waveny and the GreenLink close at dark, so short November afternoons push trail runs earlier on weekdays.

The Waveny trail that is up for a decision this fall

The last trail on that list is the one most likely to change. The Waveny Park Conservancy says the Merritt Parkway Trail is exposed to the state road at several points, which spoils the woodland view and brings in traffic noise. Its approved schematic plan for the stretch from Lapham Road to South Avenue calls for selective rerouting, berms, plantings, stone walls, and a short fence.

The timing ties into this season. The Conservancy says it is working with Heritage Landscapes on detailed construction drawings. If the town approves the budget in the fall of 2026, Phase One could begin in 2027, followed by work over several years. NewCanaanite reported a target start of spring or early summer 2027, with the existing trail staying in place during the project. Anyone training at Waveny this November is running on a trail whose next few years depend on budget votes happening now.

A Main Street shop that leads with apparel

For the first time, the season has a dedicated endurance shop downtown. The Amateur opened this summer at 70 Main St. in a former gallery space that had been empty for several years. Founder Alex Holmes described it as "essentially like a concrete white box that we could design into." The shop sells apparel and accessories for running, cycling, and skiing, but no hard goods. "Most places are hard goods first," Holmes said. "We really want to lead with apparel and accessories because that's where the white space is."

On the running side, the shop carries about 12 brands, including Bandit, Satisfy, On Running, District Vision, New Balance, Hoka, Norda, and Nike, with Adidas expected soon. Cycling brands include MAAP from Australia and Universal Colors from the UK. Alpine ski apparel arrives as winter approaches, which lines it up with the stretch between the Turkey Trot and the Santa Run. Holmes said the shop is for intentional athletes, not necessarily elite ones. "Performance doesn't mean elite," he told NewCanaanite.

The Amateur already hosts runs and rides from the store. The first came together through his wife's running team, and Holmes said more are on the way. Events are announced on the store's social media, newsletter, and website. The shop is open Wednesday through Sunday, 11 a.m. to 6 p.m.

Roads to plan around on the bike this month

Riders deal with the same question of surfaces, only on asphalt, and two projects matter this month. The Department of Public Works update posted October 5 lists work on Route 106, also known as Silvermine Road, between Valley Road and Canoe Hill Road, with daily closures and detours from October 7 through mid-November. The same page also says that work started September 28. Final paving on South Avenue and Farm Road is suspended until further notice. Both roads are open, but traffic may alternate one way at their intersection. Paving on Route 124, Cherry Street, Main Street, and Oenoke Ridge is finished, and crosswalk and stop-bar striping is planned for the night of Wednesday, October 7, weather permitting.

If you're lacing up for the Turkey Trot, signing the family up for the Santa Run, or just curious how the Waveny trail plan moves through this fall's budget, I'm glad to talk it through. Local seasons like this one are a big part of what I share with clients. April D Kaynor would love to hear which race you're running. Let's Connect.