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Pumpkinvine Classic

The Pumpkinvine Classic is a cycling and trail running event held on Saturday, September 12, 2026. It is located at 240 US-20 in Middlebury, Indiana.

Date:
Sat, Sep 12, 2026 at 11:59 PM
Location:
240 US-20
Middlebury, Indiana
46540
United States
OpenStreetMap Google Maps
Links:
pumpkinvine.org Register at bikereg.com
Tags:
Cycling Trail

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!

Early bird pricing ends June 30th, so sign up early and save!

More info to come including route maps! Check back soon!

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:

  • 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.

  • 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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