Explore Woodstock’s Legendary Music History on the Rock n' Roll Walking Tour
Difficulty
moderate
Duration
2–3 hours
Fitness Level
Suitable for most people with average fitness who can manage moderate walking
Overview
Discover Woodstock’s vibrant music legacy on the Rock n' Roll Walking Tour. Explore historic sites tied to legends like Bob Dylan and unwind at serene Bearsville Park on this engaging 2.5-hour journey.
Woodstock Rock n' Roll Tour
Saturdays 2 PM and Sundays at 11 AM
Select participants and date
Adventure Photos
About This Adventure
Embark on a captivating walking tour with ROCK JUNKET, exploring the rich music history of Woodstock from April to October. Discover the stories behind iconic artists like Bob Dylan and Jimi Hendrix, visit historic sites, and unwind at Bearsville Park. Experience the unique charm of this legendary town in just 2.5 hours!
SEASONAL TOUR-APRIL THROUGH OCTOBER (Saturdays at 2 pm and Sundays at 11 am)
Join ROCK JUNKET for our Woodstock music history walking tour, Learn why this small Upstate NY town inspired the name for the 1969 festival, 60 miles away. Hear stories and see sites associated with Bob Dylan, Jimi Hendrix, Todd Rundgren, The Band and more, and visit locations of famous clubs and hangouts. Learn why Woodstock has the the history of welcoming artists, musicians and eccentrics among its bucolic environment. Tour also includes a visit to beautiful Bearsville Park at 291 Tinker Street, with more history and on site bar and restaurants. A great place to end the tour and chill.
Tours offered on Saturdays at 2 PM and Sunday at 11 AM and run 2 1/2 hours with light walking. Tour meet up spot is PEACE LOVE and CUPCAKES/HAPPY LIFE PRODUCTIONS at 59 Tinker Street (NOT to be confused with 59 Mill Hill Road, which is a laundromat). Free parking suggestion is across from the Colony venue at 22 Rock City Road. Guests must provide their own transportation for Bearsville Park portion of tour, which is 3/4 of a mile down Tinker Street/Route 212. PLEASE NOTE: If Bearsville Park is unavailable due to a private function, the town tour will be extended. Also note that the Band’s Big Pink House and the 1969 Festival site are not included on this tour. Too far out, man!
Adventure Tips
Wear comfortable walking shoes
The tour involves 2.5 hours of walking on paved and uneven surfaces, so sturdy shoes are a must.
Bring a water bottle
Stay hydrated, especially on warmer days in spring and summer, as there are limited places to refill along the route.
Bring a camera or smartphone
Capture the historic sites and picturesque streetscapes as you go through Woodstock’s storied music landmarks.
Check the weather forecast
Walking tours run rain or shine but dressing appropriately ensures a comfortable experience.
Local Insights
Wildlife
- Eastern chipmunk
- Red-tailed hawk
History
Woodstock’s transformation into a music hub began in the 1960s, attracting artists seeking freedom to create away from the city.
Conservation
The town encourages sustainable tourism, promoting walking tours to protect its historic streets and minimize vehicle traffic.
Select participants and date
Adventure Hotspots in Woodstock
Frequently Asked Questions
Recommended Gear
Comfortable walking shoes
Supports long periods of walking on varied terrain during the tour.
Water bottle
Keeps you hydrated during warm-weather outings.
summer specific
Light rain jacket
Protects against sudden spring showers common in Woodstock.
spring specific
Sunhat and sunscreen
Provides protection from sun exposure during daytime walks.
summer specific