Kentucky Bourbon Trail !!NEW DATE!!

Event date: 
Thu, 09/24/2026 - 11:30am to Mon, 09/28/2026 - 1:00pm

Kentucky Bourbon Trail Ride – Sept 25–28, 2026


Ride Overview

Ride Type: Multi-Day Chapter Ride
📍 Departure Location: Woodstock Harley-Davidson
🕒 Meet: 11:30 AM | Safety: 11:45 AM | KSU: 12:00 PM

Dates: September 25–28, 2026
Route: Woodstock H-D → Bardstown → Kentucky Bourbon Trail → Louisville → Woodstock H-D
Pace: Moderate touring with scenic backroads and destination stops

Four days. Great roads. World-class bourbon. This is one of the premier destination rides of the season.

Ride Snapshot

Distance: ~1,000+ miles total
Ride Style: Touring + Backroads + Destination
Experience Level: Intermediate

Pace:
Moderate Touring Pace - 75%
Daily Distance Load:
Long Distance Days - 90%
Technical Riding:
Some Curvy Roads - 55%


Highlights: Maker’s Mark, Woodford Reserve, Four Roses, Bardstown, Louisville Whiskey Row
Route: Woodstock H-D → Bardstown, KY

Route Plan:
Primary: I-65 South for efficient travel
Final stretch: Bluegrass Parkway into Bardstown

Expected Arrival:
Approximately 7:30–8:30 PM with fuel and stretch stops included

Rider vs RV Coordination:
Riders: Group ride departs from Woodstock H-D
RV Crew: Recommended earlier departure around 9:00–10:00 AM, direct to Bardstown basecamp

Evening:
Casual dinner, no scheduled activities, and time to reset for the riding days ahead.
Morning Ride:
KY-49 → KY-52 scenic loop

Distillery Stop:
Maker’s Mark
Target arrival: 2:00–3:00 PM

Evening:
Dinner in Bardstown and a relaxed night. Saturday is the big signature ride day.
Morning Ride — Best Roads of the Trip:
Old Frankfort Pike
McCracken Pike
Kentucky horse farm country

Planned Stops:
1. Woodford Reserve — approximately 11:00 AM
2. Four Roses Distillery — approximately 2:30 PM

Transfer Ride:
Cruise into Louisville, approximately 1 hour

Evening — Whiskey Row:
Walkable stops may include Angel’s Envy Distillery and Old Forester Distilling Co.

Bikes parked, boots on the ground.
Morning:
Breakfast downtown
Optional quick distillery visit if timing allows

Ride Home Options:
Direct: I-65 North
Scenic Add-On: Southern Indiana backroads

Plan for a full travel day returning to Woodstock H-D.
Bardstown — Nights 1–2:
Talbott Tavern — historic, bourbon vibe
Hampton Inn Bardstown — clean, easy, good parking

Louisville — Night 3:
Moxy Louisville Downtown — fun, social, walkable
Omni Louisville Hotel — premium downtown option
  • Arrive packed, fueled, and ready to ride
  • Prepare for multi-day riding and long highway stretches
  • Check the chapter app or website for weather updates
  • Bring rain gear, layers, hydration, overnight essentials, and valid ID
  • Book hotels early once lodging details are finalized
  • Distillery tours may require advance reservations
  • No alcohol during official ride time
  • Return route or dismissal plan will be reviewed during the ride briefing

Road Captain Notes

This is a structured multi-day ride combining highway travel, scenic Kentucky backroads, distillery visits, group meals, and city stops. Riders should be prepared for long days, group coordination, and varying riding conditions. We will review route segments, fuel strategy, communication, lodging logistics, and expectations prior to departure.

Explore official Bourbon Trail info, maps, distillery details, and tour planning resources.

Event location:

Bardstown KY

Closed Event: Chapter activities are conducted primarily for the benefit of H.O.G. Chapter members. Closed Events are those events open to Chapter members and one guest per member.  All guests must sign an event release. Be aware, all rides and events are subject to change or cancellation due to weather or other circumstances beyond our control.

Impairment Policy: The consumption and use of alcohol is a serious personal responsibility involving the safety of family, riding friends and the individual HOG member. Alcohol consumption before or during a motorcycling activity is not safe, responsible behavior. Woodstock Chapter #5668 does not allow the use of alcohol or drugs before or during a riding event* and does not furnish alcohol at Chapter rides. Riders whose skills are observed or suspected to be impaired by alcohol or drugs before riding cannot join the ride. Riders using alcohol or drugs while riding will be asked to leave the ride. It is the responsibility of each Template Chapter member to support the consistent enforcement of this policy

Photography Policy: Photographing, filming, recording and videotaping of activities and events will be occurring Woodstock Chapter events. By entering the H.O.G.® event area, you irrevocably grant permission to the Harley-Davidson Motor Company® and its agents to photograph, film, record and/or videotape you and use (and authorize the use of) your name, image, likeness, voice, and/or biographical or other information in any and all media now known or hereinafter developed in perpetuity for any and all purposes.

Event Coordinator: 
Chris Roddick
Head Road Captain