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4 swimming, duathlon, running, and other events in Middlebury, Connecticut

From big races to Saturday morning group runs—find swimming, duathlon, running, and triathlon events and connect with the local endurance sports community.

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Middlebury

4 events in Middlebury
  • Sat, Jun 20, 2026 at 7:00 AM

    Welcome! I’m your Race Director, Tom Wilkas. We are pleased to bring you both the original Pat Griskus Sprint Triathlon, which started in 1987, and the Olympic distance race, which was conceived in 2002. Since then, we have also added a duathlon and a second sprint triathlon run concurrently with the Olympic triathlon.

    Key folks include: Dave Heller, Robin Griskus, Laura Griskus, Marty Cashin, Mike Maximenko, Dave Kunces, Kim Tessier, Jeff Sheldon, Tom Hill, Jim O’Rourke, Chris Hibbs, Sandra Heller, Kristin Heller, Meghan Curley, Tim Cipriano, Tim Ruh, Karen Mcwhirt, Rob Scott, Eric Pattison and Others. Pat Griskus was an amazing guy and credited with paving the way for the many amputee athletes to follow.

    Both races are USAT Sanctioned and are held at Quassy Amusement Park on Route 64 in Middlebury, CT. The Sprint distance starts with a half-mile swim in spring-fed Lake Quassapaug, enjoy the challenging 10.5 mile bike around the lake, and the out-and-back 3.1 mile run. There is a First Timers division for those tackling their first Triathlon ever, with medals for all first time finishers. With close to 100 first-timers each year, this race has become a favorite for first time triathletes!

    The Olympic distance race features a clean and clear one mile lake swim in Lake Quassapaug, enjoy a 25 mile challenging one loop bike course through classic New England farm country, and a 6.2 mile run on shaded back roads.

    See full details
  • Sat, Jun 27, 2026 at 7:30 AM

    ake Quassapaug is a 296 acre lake situated in Middlebury, CT. Quassy Amusement Park, Lake Quassapaug, Rt. 64 (2132 Middlebury Road) Middlebury, CT 06762 | P.O. Box 887 1-800-FOR-PARK or 203-758-2913 Fax: 203-598-7261 | [email protected] www.quassy.com Quassy was founded as an amusement park in 1908, sitting on the south shore of Lake Quassapaug in Middlebury, Connecticut. On 20 plus acres, it boasts 22 amusement rides, a new Splash Away Bay Water Park and the beautiful Quassy beach. Water Quality Information: http://www.ct.gov/caes/cwp/view.asp?a=2799&q=488556 Changing into or out of swimsuits other than in locker rooms or other designated areas is prohibited. Meet Management may restrict access to specific competition areas, including the start, competition course, and finish areas. Only athletes, coaches, officials, and official meet staff actively participating in the meet shall be permitted in these areas. All coaches must present a valid USA Swimming coach card to the Meet Director prior

    to the commencement of any sanctioned swim meet, and must have this card with them to enter restricted areas of the race venue.

    Event details and schedule

    Open to all FULL USA Swimming member athletes registered prior to first day of the meet. • Must be a registered Full USA Swimming athlete to enter. • A one-day CT Swimming/USA Swimming Membership registration is available for this event, but it MUST be completed prior to event day. No event-day USA/CT Swimming registrations will be permitted. See “Individual Entries” below. 1-day registration is NOT valid for the 5K. • Age on June 27, 2026 will determine age for the meet. Recommended entry standards: • For 12 and under events, Minimum of BB time standard in the 500yd freestyle or the 400M freestyle or successfully completed a minimum of a 500M open water swim in a bay, river, lake or at a beach. • For 13 - 14 and 15-18 events: Minimum of an A time standard in the 1000yd, 1650yd, 800M, or 1500M freestyle or successfully completed a minimum of a 1K open water in a bay, river, lake or at a beach. • For Senior/Open Event: Minimum of a AA time standard in the 1000yd, 1650yd, 800M, or 1500M

    freestyle for 15-18 Age Group or successfully completed a minimum of a 1K open water in a bay, river, lake or at a beach. • Athletes not completing the 5K within 1 hour and 30 minutes may be removed from the course at the discretion of Meet Management

    See full details
    Open WaterSwim via Active.com
  • Sat, Jun 27, 2026 at 7:30 AM

    CSI Open Water Championship | Connecticut Swimming | Connecticut Swimming

    1k2.5k5kOpen WaterSwim via RunSignup
  • Sat, Sep 26, 2026 at 9:00 AM

    Race Date: Saturday, September 27, 2025

    Location: Pies & Pub, One Store Road, Middlebury, CT

    Benefiting: American Cancer Society's Making Strides Against Breast Cancer

    Registration Fees:

    • Early Bird (Before August 1): $35

    • Kids under 12 : $25

    • Standard (August 1 – September 26): $40

    • Day of Race (September 27): $40

    Perks for Participants:

    • Free Race T-Shirt: Register by August 31, 2025, to receive a complimentary t-shirt.

    • Free Pizza: All participants enjoy delicious pizza courtesy of Pies & Pub.

    • Free Beer: Participants aged 21 and over receive a complimentary beer.

    To ensure a smooth start, here's the key info on bib pickup, parking, and race day:

    Bib Pickup:

    • Tomorrow, Friday, September 26th: Swing by Pies & Pub (1 Store Road, Middlebury, CT) from 4:00 PM to 6:00 PM during our Hops For Hope Happy Hour—grab your bib, t-shirt (if registered in time), and get in the spirit early!

    • Race Day (Saturday, September 27th): Pickup available starting at 8:00 AM at Pies & Pub, right before the 10:00 AM start. We recommend arriving early to avoid any last-minute rushes.

    Race Day Parking:

    Help keep things flowing smoothly for everyone—here are the best spots:

    • Across the street at the Vyne Restaurant lot.

    • At Smokey the Bear behind Pies & Pub.

    • On the streets near Westover School.

    • For a great warm-up option: Park at Meadowview Park Playground and stroll along the greenway to the start line—it's a scenic way to get those legs ready!

    Please avoid parking at the Middlebury Plaza, as local businesses rely on those spaces for their customers. Parking could be difficult and limited if you arrive last minute, so please come early on September 27th and give yourself plenty of time to park and get to the race start at Pies & Pub by 10:00 AM.

    Perks & Gratitude:

    All participants will enjoy free pizza, and those 21+ can savor a complimentary beer—special thanks to Pies & Pub and Counter Weight for their generous donations! Speaking of support, we’re deeply grateful to all our sponsors. Special Thanks to Major Sponsor: Connecticut Investment Advisors. Your contributions make this event possible!

    Stay Updated:

    Visit piesandpub.com for any last-minute info, or check our Facebook page https://www.facebook.com/Piesandpintstatatrot/ after the race for results. We can’t wait to see you tomorrow and Saturday!

    Spread the Word:

    It’s not too late—tell your friends to join us! They can sign up at https://runsignup.com/Race/CT/Middlebury/PiesPubTaTaTrot5k and be part of this incredible community effort.

    Race Map: Check out the course details with this QR code or visit https://ridewithgps.com/routes/52793047.

    Let’s paint Middlebury pink and trot toward hope together!

    With gratitude and excitement,

    The Pies & Pub Ta-Ta Trot Team

    Supporting Making Strides Against Breast Cancer

    #TaTaTrot5K #MiddleburyStrong

    See full details
    5kRun via RunSignup

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