October might be Lexington’s richest month of the year — Washington and Lee’s Parent and Family Weekend brings the whole town to life, harvest festivals pop up across Rockbridge County, and downtown wraps up the month with Halloween festivities. Here’s exactly what’s happening, when, and how to get there without worrying about parking or driving home after dark.
Parent and Family Weekend at Washington and Lee — October 2–3
W&L’s Parent and Family Weekend fills Lexington’s hotels and restaurants for the first weekend of the month, with a full slate of campus concerts at the Lenfest Center — a Choral Concert on Friday, October 2, and an Instrumental Concert on Saturday, October 3. If you’re visiting for the weekend, expect downtown to be busy and parking tighter than usual.
The same weekend, Rising Appalachia plays a bonus show at Lime Kiln Theater on Saturday, October 3 — already sold out, but worth checking the waitlist if you’re hoping to catch it.
Harvest Season at Rockbridge County Wineries & Farms
Saturday, October 3 — Rockbridge Vineyard & Brewery Fall Harvest Festival, Raphine. An annual fall tradition at one of the area’s longest-running wineries, combining harvest-season festivities with wine and craft beer.
Saturday, October 3 — McCormick Farm Open House, Raphine. A historic working farm open to visitors for the day.
Saturday, October 10 — October Uncorked at Ecco Adesso Vineyards, Fairfield. A fall-themed tasting event at one of Rockbridge County’s newer vineyards.
Saturday, October 17 — Annual Apple Butter Festival, Wade’s Mill, Raphine. A long-running local tradition celebrating apple season with fresh-made apple butter and fall activities.
If you’re planning a group outing across any of these — especially combining a winery stop with the Apple Butter Festival, since both are near Raphine — a scheduled ride means no one has to skip the tastings to drive. See our Lexington winery and brewery tour services for details.
Downtown Lexington: Fall Festivities
Saturday, October 3 — Apple Day, downtown Lexington. A community celebration of apple season right in town.
Saturday, October 10 — Mountain Day, Buena Vista. A beloved, long-standing local fall tradition on Magnolia Avenue.
Tuesday, October 6 — Ailey II: The Next Generation of Dance, Lenfest Center. A touring performance from Alvin Ailey’s second company, known for developing some of the dance world’s most promising young talent.
Saturday, October 17 — Sonoklect presents Jeff Coffin and CPK Trio, Lenfest Center. An evening of jazz from a Grammy-winning saxophonist known for his work with the Dave Matthews Band.
Virginia Horse Center — October Events
Sunday, October 11 — Fall Jumper Derby & Dressage Show, held on top of the hill at the Virginia Horse Center.
October 29 – November 1 — VHC Eventing Fall Recognized Horse Trial, a multi-day eventing competition closing out the month.
Multi-day shows mean extra traffic between hotels and the Horse Center grounds — book a Lexington shuttle ahead of time if you’re attending across the full weekend.
Halloween in Lexington
Friday, October 30 — Downtown Lexington Trick or Treat, Main Street. A family-friendly Halloween tradition through the heart of downtown.
Saturday, October 31 — Spooktacular, Magnolia Avenue, Buena Vista. A community Halloween celebration to close out the month.
Saturday, October 31 — Concert Guild presents “Baroque to Broadway” with soprano Penelope Shumate, Lenfest Center — a different kind of Halloween evening for those who’d rather hear a concert than hand out candy.
Quick Reference: October 2026 Lexington Events
| Date | Event | Location |
| Oct 2 | W&L Parent Weekend: Choral Concert | Lenfest Center |
| Oct 3 | W&L Parent Weekend: Instrumental Concert | Lenfest Center |
| Oct 3 | Rising Appalachia (sold out) | Lime Kiln Theater |
| Oct 3 | Rockbridge Vineyard & Brewery Fall Harvest Festival | Raphine |
| Oct 3 | Apple Day | Downtown Lexington |
| Oct 3 | McCormick Farm Open House | Raphine |
| Oct 6 | Ailey II: The Next Generation of Dance | Lenfest Center |
| Oct 10 | Mountain Day | Buena Vista |
| Oct 10 | October Uncorked | Ecco Adesso Vineyards, Fairfield |
| Oct 11 | Fall Jumper Derby & Dressage Show | Virginia Horse Center |
| Oct 17 | Annual Apple Butter Festival | Wade’s Mill, Raphine |
| Oct 17 | Sonoklect: Jeff Coffin and CPK Trio | Lenfest Center |
| Oct 29–Nov 1 | VHC Eventing Fall Recognized Horse Trial | Virginia Horse Center |
| Oct 30 | Downtown Lexington Trick or Treat | Main Street |
| Oct 31 | Spooktacular | Buena Vista |
| Oct 31 | Concert Guild: “Baroque to Broadway” | Lenfest Center |
FAQ
Is Lexington busy during W&L’s Parent and Family Weekend?
Yes — the first weekend of October is one of the busiest of the fall, with hotels filling up and downtown restaurants at capacity. Booking transportation in advance is a good idea if you’re visiting for the weekend.
Can I combine a winery visit with the Apple Butter Festival in one trip?
Yes — several of the harvest events, including the Rockbridge Vineyard Fall Harvest Festival and the Apple Butter Festival at Wade’s Mill, are near Raphine, making it easy to combine stops with a scheduled ride.
Is there shuttle service for multi-day events at the Virginia Horse Center?
Yes — we run scheduled and on-demand routes between Lexington-area hotels and the Horse Center throughout events like the VHC Eventing Fall Recognized Horse Trial.
Can I book a group shuttle for a wedding or private event during a busy October weekend?
Absolutely — with Parent and Family Weekend, multiple festivals, and Halloween events throughout the month, October is one of the busiest months of the year locally. See our wedding transportation services for details.
Missed last month? Check out our September 2026 Lexington Events Guide.
Ready to book? Contact Traveller Shuttle Services or call (540) 784-4022 for availability.
