Photo: Hayden Soloviev · CC BY 4.0
Waterbury · United States

Cycling & running events in Waterbury, 2026

414events this year

414 races within 80 km of Waterbury

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A few races to know in Waterbury

We all need a goal — why not think big? Pick one and start training for it. Already happened this year? Find some practice races to build toward next year's edition.
Run·Road
Waterbury

MY MOTHER MADE ME DO IT 1 Mile Mother's Day Race

My Mother Made Me Do It is a Mother's Day 1-mile run/walk held at Hotchkiss Field in Prospect, Connecticut. The event begins at 9:00 AM. Packet pickup starts at 7:30 AM, and awards and post-race activities commence at 9:30 AM. The field is limited to 130 participants, making it a small local race. The course consists of two laps on the cinder walking path encircling the park. Walkers and runners use the same path. On-site parking is available. Awards are presented to the overall female, male, and non-binary winners, along with the top three finishers in age groups ranging from 12-and-under to 80-plus. Shirts are guaranteed for those who register by the cutoff date. O2 Event Productions is the organizer.

Road
Run·Xc
Waterbury

Westover Cross Country Meet

Listed in our event index as Westover Girls Cross Country Meet.

Xc
Run·Xc
Waterbury

NVL Cross Country Championship

Listed in our event index as NVL Cross Country Championship.

Xc
About cycling & running in Waterbury

Waterbury-Shelton Training Notes

Running: Waterbury-Shelton runners get a practical menu of road miles, trail days, and race-course Sundays. The route covers 39 km while gaining +270 m. The Y Running Program brings the group structure. Weekday runs leave from the Waterbury YMCA front steps at 136 West Main Street. Sunday runs move offsite and sometimes use racecourses. Coach-led sessions hit long runs, speed work, hill repeats, and faster Level 2 pacing. Oh Boy 5K, FreeFromEvil 5k Race/Walk, Soul n Body Thanksgiving Trail Run, and Tom Centinaro Memorial "Dam" Race give the calendar its anchor event feel.

Cycling: Waterbury-Shelton riding leans serious without getting fussy. The Greater Waterbury YMCA Tri Club supports multisport and single-sport athletes, and the club runs weekly outdoor bike rides. The route covers 3 km and gains 1,340 m on mostly paved roads. That route is 97% paved and 3% unpaved, so it feels like base miles with a little bite. The climbs are north, and the riding keeps getting better as you go farther north toward Sheffield. 39 km.

Season: The brief does not name best months, so locals build the season around the clubs, the race list, and whatever fitness block is on deck. Summer training stays simple when runners use weekday YMCA starts, Sunday offsite runs, and racecourse reps for sharpening. Riders can keep Z2 on the paved routes, then use the northbound climbs for strength work before a gran fondo or hard club day. Winter changes the mindset more than the map. The same road loops, trail runs, and mixed-surface options remain the reference points, but runners and cyclists pick sessions with more care when daylight and conditions tighten.

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Coming soon in Waterbury

All races within 80 km, sorted by date. Click any event for the route, registration link, and past results.
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What runners & riders are signing up for

If you're traveling — or just curious — here's where the action is across two of the most active markets on TrainerDay.