Trolley Redefined

When trolleys were first invented, they were on rails, transporting goods and people long before public transportation switched to buses and trains. Yet, the nostalgic trolley is still here in Southern Delaware!  

Not on rails, however – the Jolly Trolley travels the roads on its Fixed Route Shuttle service with stops along the way between Rehoboth and Dewey. With convenient stops located throughout Rehoboth & Dewey Beach Guests may travel back and forth between destinations as a couple or a group. Best thing? You can relax and forget about finding that precious parking space on a busy night! 

The Jolly Trolley has become an iconic sighting on summer days on their main route between Rehoboth and Dewey beaches since its inception more than 50 years ago. Owned by the local Hastings family who has taken the services to an entirely new level since 1992 with year-round reservations and charter services to provide safe and reliable transportation to your destination airport or other event locations. 

Professionally licensed & insured, Jolly Trolley transportation services offer driving services for groups large or small, ensuring your arrival at your destination without the hassle and often confusing details of parking.  

Escorting everything from bridal parties to beach commuters that just don’t want to deal with the Coastal Highway, the Jolly Trolly charter services gets people where they need to be – safely and parking meter free.  

Check out their fleet of available vehicles available for reservation your next outing or special event! From the luxurious Lincoln to travel in style to the airport or dinner, to the Jolly Bus, which can hold up to 34 people including luggage and other vehicle sizes in between, there’s sure to be a Jolly Trolley vehicle to fit your travel needs, but of course reservations well in advance for their charter services are recommended. 

Wedding parties, bachelorette parties, winery or brewery tours are all popular options with this safe and reliable transportation service that continues to receive accolades for its professionalism, vehicle cleanliness and friendly customer service. 

Check out their website, which explains not only their available charter services, but their Fixed Route Shuttle Trolley Schedule and Route Map which runs from Memorial Day Weekend through Labor Day. 

The Jolly Trolley Fixed Route Shuttle service between Rehoboth & Dewey Beach provides a safe way to travel and negotiate through the beach traffic without the stress of unpredictable traffic. The trolley provides reliable transportation for its passengers for a nominal fee (compared to other services such as Uber or Lyft).  

For only $3 one-way, or $5 round trip, tickets can be purchased on site or on their online format for purchase

Jolly Trolley is also renowned for its partnerships with other local destinations, hotels and B&Bs and special event transportation. So the next time you’ve got a simple trip from Rehoboth to Dewey in mind, or an excursion to Dogfish Head Brewery’s Milton location, give them a call and find out just how reliable and trustworthy their service is.  

Have a Jolly Trolley time!  

BY Bridget Fitzpatrick, Resident Journalist

Sign up for our e-news updates!

Skip to content