The Woodstock: Rock N’ Roll History Tour offers a unique opportunity to explore the legendary town’s enduring musical legacy. This captivating 2.5-hour guided experience delves into the stories of iconic artists who have graced Woodstock, from Bob Dylan to Janis Joplin and Jimi Hendrix. With knowledgeable guides leading the way, participants can discover the town’s significant sites, including Dylan’s songwriting haven, The White Room. For those seeking to uncover the deep-rooted influence Woodstock has had on rock ‘n’ roll, this tour promises an insightful and engaging journey. But the true marvel lies in what awaits beyond the tour’s conclusion, as the town’s timeless enchantment continues to captivate music enthusiasts from around the world.
Key Points

- A 2.5-hour guided music-focused tour exploring Woodstock’s rich musical heritage, featuring stories of iconic artists like Bob Dylan, Janis Joplin, and Jimi Hendrix.
- Highlights include visiting historic sites that shaped rock n’ roll, such as Bob Dylan’s songwriting spot, The White Room.
- The tour starts at Peace, Love & Cupcakes on Tinker Street and ends at Bearsville Center, with guests responsible for their own transportation.
- Engaging commentary from knowledgeable guides, providing insights into Woodstock’s counterculture movement and the 1960s rock ‘n’ roll revolution.
- Overall positive customer feedback, with a 4.7/5 rating, praising the friendly and informative tour guide.
Tour Overview

The Woodstock: Rock n’ Roll History Tour is a 2.5-hour guided music-focused experience that allows visitors to discover the rich history of Woodstock, New York.
Priced from $46.64 per person, the tour runs seasonally from April through October, with Saturday and Sunday departures. Guests can reserve their spot and take advantage of the pay-later option.
The tour starts at Peace, Love & Cupcakes on Tinker Street and ends at Bearsville Center, with guests responsible for their own transportation.
Cancelations are free up to 24 hours in advance, ensuring flexibility for visitors.
You can also read our reviews of more tours and experiences in New York State.
Tour Experience

The guided Woodstock: Rock n’ Roll History Tour focuses on the rich musical heritage of the town.
Guests will discover the music history of Woodstock and hear captivating stories of iconic artists like Bob Dylan, Janis Joplin, Jimi Hendrix, and more.
The tour highlights:
- Historic sites that shaped the Rock n’ Roll scene
- The White Room, Dylan’s famous songwriting spot
- Locations associated with The Band, Todd Rundgren, Muddy Waters, and other Woodstock legends
- The final resting places of renowned musicians
- Engaging commentary from a knowledgeable guide about Woodstock’s influential music culture.
Starting and Ending Points

The tour commences at Peace, Love & Cupcakes located at 59 Tinker Street, where guests gather before embarking on their musical journey through Woodstock.
From there, the group makes its way to the historic Bearsville Center at 291 Tinker Street, approximately a quarter-mile walk.
Guests are responsible for providing their own transportation from the starting point to the end point, which takes only around four minutes to cover on foot.
The tour’s diverse highlights showcase Woodstock’s rich musical legacy, allowing participants to enjoy the stories and sites that shaped the town’s iconic rock ‘n’ roll heritage.
Transportation

Guests are responsible for providing their own transportation from the starting point at Peace, Love & Cupcakes to the ending point at Bearsville Center, a short 4-minute walk covering approximately a quarter-mile distance. This allows participants to explore the town of Woodstock at their own pace before and after the tour.
Key transportation details include:
- Guests should plan to park in the free Comeau Drive parking lot, across from the Woodstock police station.
- The tour guide will provide clear directions to navigate the short walk from the starting to ending points.
- Participants should wear comfortable shoes and be prepared for the walking portion of the tour.
- The tour doesn’t include transportation to the 1969 Woodstock Festival site or The Band’s studio, Big Pink.
- Guests are responsible for any additional transportation needs beyond the tour route.
Meeting Point
Participants should plan to park in the free Comeau Drive parking lot, located directly across from the Woodstock police station at 76 Tinker Street. This is the designated meeting point for the Woodstock: Rock N’ Roll History Tour.
From here, the guided walking tour will commence, allowing guests to explore the historic sites and landmarks that shaped the legendary Woodstock music scene. The tour guide will provide invaluable insights and engaging stories, transporting participants back in time to the golden era of rock and roll in this iconic town.
After the tour, guests will make their own way to the final destination, the Bearsville Center, just a short 4-minute walk away.
Tour Inclusions
Included in the Woodstock: Rock N’ Roll History Tour are a guided walking tour and all necessary tips and gratuities.
The tour features:
- Exploration of the town’s rich musical heritage
- Visits to sites associated with legendary artists like Bob Dylan, Janis Joplin, and Jimi Hendrix
- Insights into the vibrant Woodstock music scene and its lasting impact
- Engaging storytelling from a knowledgeable guide
- The opportunity to walk in the footsteps of iconic musicians and discover the town’s enduring musical legacy.
With these inclusions, the tour provides a comprehensive and immersive experience for music enthusiasts seeking to uncover the captivating history of Woodstock’s rock and roll roots.
Noteworthy Locations

The tour takes visitors to several noteworthy locations that played pivotal roles in Woodstock’s rich musical heritage.
At the White Room, travelers can envision Bob Dylan penning some of his most iconic songs. The tour also explores sites connected to other Woodstock legends like Janis Joplin, Jimi Hendrix, and Muddy Waters.
Plus, guests visit the final resting places of these influential artists. Through these stops, the tour provides an immersive experience, allowing participants to gain a deeper understanding of how Woodstock became a hub for the counterculture movement and the epicenter of the 1960s rock ‘n’ roll revolution.
Customer Feedback

Visitors have consistently praised the Woodstock: Rock n’ Roll History Tour for its engaging and informative experience.
The tour boasts an overall rating of 4.7/5 based on 3 reviews. Positive comments highlight the tour’s friendly and knowledgeable guide, Larry, who provides invaluable information and engaging storytelling about the Woodstock music scene.
Guests appreciate the great overall experience, which offers historical insights and photographs.
Key highlights of the customer feedback include:
- Friendly and knowledgeable guide
- Engaging storytelling about Woodstock music history
- Invaluable information about notable locations and figures
- Great overall experience with historical context
- Informative tour that exceeds expectations
Frequently Asked Questions
Is the Tour Wheelchair Accessible?
The tour appears to be wheelchair accessible, as the meeting point has a free parking lot and the starting and ending points are within a short walking distance. However, it’s best to confirm this directly with the tour operator.
Can Participants Take Photos During the Tour?
Participants are generally allowed to take photos during the tour. However, it’s advisable to check with the tour guide beforehand as there may be restrictions at certain historical sites or locations to preserve the experience.
What Is the Dress Code for the Tour?
The tour does not have a strict dress code. Guests can dress comfortably in casual attire suitable for a walking tour. It’s recommended to wear comfortable shoes as the tour involves walking around historic Woodstock sites.
Can the Tour Be Customized for Special Interests?
Many tour companies allow customers to customize tours to suit their special interests. The Woodstock: Rock N’ Roll History Tour could likely be tailored for visitors focused on specific artists, songwriting, or other unique aspects of music history.
Are There Any Food or Drink Options Available During the Tour?
The tour does not include any food or drink options. Guests are responsible for arranging their own refreshments before or after the tour. Some local cafes and restaurants are available near the starting and ending points.
Recap
The Woodstock: Rock N’ Roll History Tour offers an engaging and informative exploration of the town’s rich musical legacy. With knowledgeable guides, participants can discover the stories behind iconic artists and visit significant sites like Dylan’s songwriting haven. For just $46.64, this 2.5-hour guided experience provides valuable insights into Woodstock’s enduring influence on rock ‘n’ roll, making it a must-do for music enthusiasts.
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