Private Walking Tours

Interested in going out and about a charming and historically rich town? Book a private walking tour with Rye Historical Society! 

Gather your group and choose from one of three special tours:

1.) Downtown Rye 

Discover Rye’s rich and varied history by walking through downtown Rye. The tour will provide a special snapshot of Rye from its earliest days as a Native American homeland to its present as a beloved coastal community. Strolling around downtown Rye, from the Square House to the train station, learn how Rye has been a hub of significant historical events since 1660 and how Rye has been a true representation of American history.

2.) Little Dublin

Explore the rich Irish heritage of Rye with a guided walking tour through the historic "Little Dublin" neighborhood. Delve into the stories of immigration, the struggles and triumphs of the Irish community, and their profound impact on the development of West Rye.  

3.) Milton

On this fascinating journey of Rye's prime coastal area, learn about the history of Native American communities, as well as the story of early European settlement. Examine how waterways significantly impacted Rye's growth and how the New Haven railroad transformed the area from a sleepy maritime village to a sought-after summer retreat for the titans of the Gilded Age. 

Tour Fees

Non-Member $30/person

Member $25/person 

Minimum 6 participants - Maximum 15 participants

Tour Details

  • Each tour runs approximately 1.5 hours and is open to all ages. Most portions of each route are handicapped accessible. 

  • To ensure the tours are exclusive to your group, groups should be a minimum of 6 participants and maximum of 15 per tour session. For groups more than 15, we may schedule your tour on multiple dates. We respectfully request that final group numbers must be confirmed at least 1 day in advance of the scheduled date. 

  • Tours are available for scheduling Tuesdays through Saturdays between 9am-4:00pm. Booking must be done at least two weeks prior to the scheduled date. 

  • Participants should wear comfortable and weather-appropriate clothing. Tours run rain or shine. In the case of severe weather, an alternative date may be set. 

  • Payment is due one full week prior to the tour. 

Submit your request here: