2 cycling, fun run, and running events in Middlebury, Indiana
From big races to Saturday morning group runs—find cycling, fun run, and running events and connect with the local endurance sports community.
Middlebury
2 events in Middlebury-
Sat, Jun 27, 2026 at 8:00 AMSee full details
Register through EVENTLINK https://websites.eventlink.com/s/northridge-middle-school-raiders/Registrations
On Saturday, June 27, 2026, the Middlebury Summer Festival 5k and 1 mile race will be taking place as part of Middlebury's Annual Summer Festival celebration. Proceeds from the race will support Northridge Middle and High School Cross Country programs.
The event will feature two races designed for runners of all ages and experience levels. We will kick things off at 8:00 a.m. with the 1 Mile kids run and competitive 1 mile for 13 and older runners. The race will begin on State Street in Middlebury, by East Park. At 8:30 am, the 5K begins. Immediately following the race, prizes will be awarded to the top three men and women overall, and the top 3 winners in each age division. Both races will be electronically timed by Watt's my timing.
NO REFUNDS!
Shirts will be unisex. Kids will be unisex youth shirts. Online registration will be available through race morning until the race starts.
Registration and check-in for both races start at 6:45 am and will be at East Park. Packet pickup on Friday will be 6-8 pm at East Park.
Please arrive early to get good parking spots around town, map of spots will be posted in the near future.
Awards for 5k: 1st, 2nd, and 3rd overall Male and Female.
If you win and BREAK current course record in 5k you will earn $100. Male record: 14:27 Benard Kiptoo Koech, Female record: Haylee Hile 18:49. We will do prize drawings as well.
If you win and BREAK current course record in competitive 1 mile you will earn $50. Male record: 4:45 Mathew Keitany, Female record: Rachel Hall 5:46
5k Age groups: Top 3 in age groups M/F
Age groups are: 14 and under, 15-19, 20-29, 30-39, 40-49, 50-59, 60-69, 70+
1 mile fun run: Awards to top 5 boys, and top 5 girls.
Kids 5 and under need an adult with them during the 1 mile run. Thank you!
1 Mile competitive mile: Awards to top 5 male, and top 5 females.
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Sat, Sep 12, 2026 at 11:59 PMSee full details
Welcome to the 2026 Pumpkinvine Classic!
The Pumpkinvine Classic is back for it's 25th year! Starting and ending at Das Dutchman Essenhaus, in Middlebury, IN, riders can enjoy the crisp fall air while touring the Pumpkinvine Nature Trail, the MapleHeart Trail and the scenic countryside. This year, there will be extended on-trail options allowing cyclists to continue beyond Abshire Park in Goshen all the way to Studebaker Park in Elkhart as well as some longer road routes for those looking to get a bit further afield! Then, everyone will finish up with a hot lunch and amenities back at Essenhaus. There will also be a variety of festivals and goings-on in the area, so check out the lodging options below. Come for the ride and stay for the weekend!
For more events in the area, check out the Elkhart County CVB and the LaGrange County CVB!
Route Maps:
Select each route tab for a preview, then choose ‘view full’ to view elevation profiles, SAG locations and open times, etc. These routes are subject to change between now and ride day, and the most up-to-date route files will be sent out in the rider info emails.
A few route notes:
-Riders can start the Pumpkinvine Full Ride and Full Enchilada routes in either direction (east or west) when leaving Essenhaus. The maps above show a westbound start, but the choice is yours!
-Riders taking on the B.E.C. Route: Due to staffing and volunteer constraints, if you want to take on the B.E.C. 100 mile route, you will need to be prepared to ride a roughly 15mph average to be able to hit all of the SAG open times. Please prepare accordingly. Because of that, feel free to leave earlier than the stated start time of 8AM, knowing that your first rest stop option at Studebaker Park (mi 22) opens at 8:30.
-These routes are subject to change between now and ride day, and the most up-to-date route files will be sent out in the rider info emails.
The Pumpkinvine Classic is a fundraising event to support the development and maintenance of the Pumpkinvine Nature Trail through the work of the Pumpkinvine Trails Coalition, a 501(C)(3) based in Elkhart County.
Lodging:
There will be a block of rooms available to rent at a discount in Middlebury and in Shipshewana. To book a room at either location, CALL (don't book online) and let them know you're ‘participating in the Pumpkinvine Classic’ to receive the group rate:
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Middlebury - Das Dutchman Essenhaus Inn & Conference Center - (574) 825-9471 - Must book on or before August 10, 2026 to get the discounted rate. Essenhaus has availability Friday and Saturday nights. This is the location of the start/finish for all routes as well as where the after-ride meal will be held.
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Shipshewana - Bluegate Garden Inn - (260) 768-4725 - Must book on or before August 9, 2026 to get the discounted rate. The Bluegate only has rooms blocked for Friday evening. Located in downtown Shipshewana, the Bluegate is blocks away from the Shipshewana trailhead of the Pumpkinvine Nature Trail, allowing you to ride to the start in Middlebury if you'd like! The Bluegate only has rooms blocked for Friday evening.
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Local Clubs & Organizations
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Club
USA Swimming Club. 91 members.
[email protected] +1 574-971-1430