TOURS - Old Stone City Trolley

90-Min Historic Kingston Tours

Step back in time aboard our signature historic trolley tour through one of New York’s oldest and most fascinating cities.

Journey through Kingston’s historic districts while learning about:

The Revolutionary War and the Burning of Kingston
The Stockade District
Senate House State Historic Site
Rondout Waterfront history
Bluestone industry heritage
Hudson River commerce
Sojourner Truth and Kingston’s abolitionist history
Local architecture and hidden landmarks

Our fully narrated 90-minute experience combines storytelling, scenic views, and rich history into an unforgettable ride through Kingston’s past.

City Hall Kingston NY Four Corners Kingston NY Old Dutch Church Kingston NY Senate House Kingston NY map of kingston ny historic district

Taste of Kingston Tours

Discover Kingston One Bite at a Time

Our Taste of Kingston Tours combine delicious cuisine with a unique trolley experience, showcasing some of Kingston’s favorite locally owned restaurants and culinary destinations.

Guests enjoy:

Comfortable trolley transportation between stops
Small plate tastings at participating restaurants
Opportunities to sample a variety of local flavors and specialties
Seasonal menu experiences featuring fresh Hudson Valley ingredients
Time to explore and enjoy Kingston’s vibrant dining scene

Perfect for visitors, food lovers, date nights, celebrations, and group outings.

Featured Stops May Include

Locally owned restaurants throughout Uptown, Midtown, and Downtown Kingston
Ethnic and international cuisine experiences
Waterfront dining destinations
Hudson Valley culinary partners and specialty food establishments

Custom Curated Experiences

Looking for something unique? We can help create a customized culinary tour tailored to your group’s tastes, interests, dietary preferences, or special occasion.

Craft Beverage Tours

Sip and explore Kingston’s growing craft beverage scene aboard our heritage-style trolley.

Put your keys away! Visit local breweries, distilleries, and tasting rooms with professional transportation on a heritage style trolley.

Experience Includes

Transportation between beverage destinations
Curated tasting experiences
Brew House Tour
Safe and comfortable group travel
Opportunities to meet local makers and brewers

Reserve the Trolley for your personal group experience. Perfect for:

Couples
Group outings
Birthday celebrations
Bachelor & bachelorette parties
Corporate events

Featured Experiences

Brewery Tours
Distillery Tastings
Seasonal Beverage Events

Please note: For Craft Beverage Tours all ticket purchasers must be 21 or over and provide valid ID. Closed-toe shoes are required for the safety of our guests and at the request of our Brewery Partners. No exceptions.

A few of our partners:

Assumption of Risk, Release of Liability, and Hold Harmless Agreement

By purchasing a ticket, participating in, or attending any Old Stone City Trolley craft beverage tour, brewery tour, winery tour, distillery tour, tasting event, or related activity, the ticket purchaser and all participants acknowledge and agree to the following:

Participants understand that alcoholic beverages may be consumed during the tour and voluntarily assume all risks associated with the consumption of alcohol, including but not limited to intoxication, impaired judgment, illness, injury, property damage, accidents, or death.

Each participant agrees to consume alcoholic beverages responsibly and in accordance with all applicable laws. Participants are solely responsible for their own conduct, decisions, actions, and behavior before, during, and after the tour, including transportation arrangements following the conclusion of the event.

To the fullest extent permitted by law, participants release, waive, discharge, and covenant not to sue Old Stone City Trolley, YRS Endeavors, LLC, its owners, officers, employees, contractors, tour guides, drivers, agents, affiliates, partner establishments, breweries, wineries, distilleries, restaurants, and property owners from any and all claims, liabilities, demands, causes of action, damages, losses, costs, or expenses arising from or related to the participant’s consumption of alcohol, intoxication, actions, omissions, negligence, injuries, property damage, or other consequences occurring before, during, or after the tour.

Participants further agree to defend, indemnify, and hold harmless Old Stone City Trolley, YRS Endeavors, LLC, and all participating craft beverage establishments from and against any claims, demands, liabilities, damages, losses, costs, attorney’s fees, and expenses arising out of or related to the participant’s conduct, actions, behavior, or consumption of alcoholic beverages.

By purchasing a ticket, the purchaser represents and warrants that all participants are at least twenty-one (21) years of age and legally permitted to consume alcoholic beverages. The purchaser acknowledges that the purchase of a ticket constitutes acceptance of these terms on behalf of all participants included in the reservation.

If any provision of this Agreement is found to be invalid or unenforceable, the remaining provisions shall remain in full force and effect.