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  • Distance: 20.8 km from City of Middletown
    Sat, Jul 18, 2026 at 8:30 AM

    Join Us for the 6th Annual George Washington Day 5K & Fun Run!

    Mark your calendars for Saturday, July 18, 2026, and take part in The Warwick Historical Society’s George Washington Day 5K & Fun Run in Warwick, NY. This exciting event features a USA Track & Field Certified 5K course (certified in 2023), offering a fast and accurate route for all participants.

    Race Details:

    Start Time: 8:30 AM

    Start Format: Self-seeded start from the official START/FINISH arch

    Timing & Scoring:

    Overall winners are determined by gun time

    Age-group awards are based on chip time

    Professional Timing: This event is chip-timed by Second Wind Race Timing

    🚨 Please note: Early starts are NOT permitted for any participants, including runners and walkers. 🚨

    Don’t miss this opportunity to race on a certified course and be part of a historic event!

    See full details
    5kFun RunRunWalk via RunSignup
  • Distance: 23.9 km from City of Middletown
    Sat, Aug 01, 2026 at 9:00 AM

    A two day showdown of fast-rolling XC trails and winding carriage roads on an entirely closed race course. Eighty miles over two days with two entirely different courses showcasing what Stewart has to offer for mountain bikers and gravel riders alike. Show up for a single day of action or throwdown for both days and compete for the King or Queen of the Dirty Double! Two day participants will receive additional custom finisher prize, and some well-earned bragging rights.

    Gravel Course: The Gravel Course (Saturday, August 1st, 9am) consists of three 13 mile loops with a majority of the course on fast service roads but enough single-track sprinkled in to keep the mountain bikers happy and in the pack. You're going to want some bite to your tires (38c or more), there are a few sections that will require technical skills if you want to send it. Ridge. Rd will be the only aid station but will be passed multiple times and will be the heart of the party. Please visit Race Website for more info.

    MTB Course: (Sunday, August 2nd, 9am) consists of two 20ish mile laps with fast, flowy XC trails. There are a few small sections broken up with service roads but the course is primarily single-track. Our Dirt Crew has put in a ton of work to get these trails in tip top shape for y'all, so be sure to give them a shout out. An Aid Station is available at the midway point as you start lap two.

    After Party & Accommodations: Bikeway Bicycles (628 NY 17K, Montgomery NY) will host an after party with local food trucks, vendors, raffles, music and more! Free Tent / Car Camping is available 1 mile from Finish at Bikeway Bicycles! Give a call to Bikeway Montgomery (845) 787-4082 to reserve a spot, Limited Capacity Available (50 spots).

    Parking: Parking is available to the first 250 vehicles at Stewart State Forest along Maple and New Rd. If you are attending the after party, please park behind the Coldenham Fire Dept. on Manzari Drive. Take a right out of Ridge. Rd as you leave Stewart State Forest, and an immediate left at the traffic light by the Citgo station. You will see the Fire Dept. 500ft. later off to your left.

    Apparel: (UPDATED SOON) Jersey's are available for pre-order and pick-up on race day! We will have a very limited supply available on race day, so lock in your swag today at a reduced price. If you want to pick your jersey up on race day, you need to place your order 3 weeks before race day. Otherwise, the jersey will be shipped to you.

    Race Directors: Ethan Kelly, Tim Schopen

    See full details
    CyclingGravelMountain BikingTrail via BikeReg
  • Distance: 515 m from City of Middletown
    Sat, Aug 15, 2026 at 8:45 AM

    Created in 2006 by Dave and Anna Madden, owners of Piccolo Cucina e Vino with a desire to help revitalize historic Downtown Middletown, the Marshall+Sterling R4DT is a 4 Mile run/walk on the morning of the third Saturday of August, where female participants will start ahead of males.

    4 MilesRunWalk via RunSignup
  • Myron Urbanski Memorial Park, Craigville Road, Goshen, NY, 10924, Goshen, New York, 10924, United States
    OpenStreetMap Google Maps
    Distance: 11.4 km from City of Middletown
    Sun, Aug 16, 2026 at 11:59 PM

    If you have ridden the TdG in the past, you know what a great event it is. This year we are adding an 80 mile ‘challenge’ route in honor of Tour founder Joe Fix Its 80th year in business. And we’re still bringing back:

    • The same great routes

    • The same great pre-ride nosh

    • The same great rest stops

    • The same great lunch and afterparty

    • The same great causes

    • And a great new T-shirt design (included free for anyone pre-registering before July 30th)

    AND, we're keeping prices the same as before! For more information, visit our The Orange County Bicycle Club website.

    See full details
    Cycling via BikeReg
  • Distance: 21.5 km from City of Middletown
    Mon, Sep 07, 2026 at 9:00 AM

    A beautiful country course with rolling hills. Both races start and finish together. timing Provided by Catskill Timing

    Refreshments served. Trophies for top 3 Male and Female, medal 3 deep in age categories. Cash Prizes for Top 3 Male and Female in both races

    5k5 MilesFun RunKidsRun via RunSignup
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