Spreading cheer is our favorite holiday tradition

Founded in 2014, Holiday Lights Trolley LLC is the original producer of the BYOB Holiday Lights Trolley Tours. Our founder, Molly Shaheen has always had a love and passion for the holidays, especially the many iconic holiday lights displays. As a seasoned event planner, she hoped to introduce a new experience that would spread holiday cheer with others in a unique way. She realized the holidays, lights, and festive drinks were the perfect combination for an unforgettable evening in Chicago. The BYOB Holiday Lights Trolley Tours were born.

Over the years, she has tweaked and refined the tours across the midwest, adding stops, bars, and various partnerships to offer the best experiences for our guests and make their seasons bright.

But, what Molly was most excited about was the opportunity to give back to local charities during the Season of Giving. Each year, city managers select a local charity to promote and collect items they are currently in need of. It’s a small way to pay it forward during the holiday season.

Now in our 12th year of service, our public trolley tours will be available for the 2025 season in 10 different cities: Boston, Chicago, Cleveland, Detroit, Grand Rapids, Kansas City, Philadelphia, Pittsburgh, St. Louis & the Twin Cities for guests 21 and older. We offer private tours in all cities. For the first time this year we are also offering family friendly trolleys in Detroit!

Pictured above are some of the great team members that make this event possible in 2025! Our 10 City Managers, our Lead Event Manager and our Founder.

What are you waiting for? Gather your "deerest" friends and family and eat, drink, and be merry with us this holiday season.