Discovering Maryland History Aboard a Modern Trolley
Towne Transport offers their engaging and educational Discover Annapolis trolley tour from April through early November, beginning and ending at the Annapolis Visitor Center, just a casual 10-minute stroll from our central location. The charm starts with the trolleys, whose bright red exterior and wooden-slat seats resemble the classic street cars you’d ride in San Francisco but add a touch of modern comfort with interior climate control. A modern speaker system assures that you’ll be able to hear the tour guide’s commentary, pointing out different landmarks, historical buildings, and high points of Annapolis culture as you take in the scenery of downtown Annapolis and the harbor. It’s a welcoming respite during every season, with the A/C providing relief from the midday heat in summer, and the trolley’s covered roof makes it suitable even on chilly or rainy autumn afternoons.
During the peak summer season, trolley tours are available on more days, but they are reduced to only weekends during the fall, available at 10:30 am, 12 pm, and 2 pm on Saturdays and Sundays through the first week of November. Once you square away your Annapolis getaway dates, book your Annapolis trolley tour time online to reserve your spot, as they often sell out a week or two in advance. If day-of space is still available, you can purchase a walk-up ticket on the spot from the trolley tour guide, payable by cash or check.
Trolleying Through Annapolis – Georgian Architecture, Iconic Landmarks, Waterfront Views, and Powerful Memorials
As you set off from West Street, your trolley guide will take you around State Circle, the esteemed political center of Annapolis, where you’ll see the Maryland State House and Governor’s Mansion. In addition to being the hallowed hall where the Treaty of Paris ratification ended the Revolutionary War, the State House served as the first peacetime capitol for ten months – its exterior dome as impressive as its stately interior Senate Chamber (worth visiting on a self-guided walking tour after your trip on the trolley).
Much of the trolley tour’s route through the Annapolis historic district focuses on colonial-era mansions, including the James Brice House, a National Historic Landmark and impossible to miss with its gorgeous brick exterior and distinctive tall, thin chimneys darting up from the rooftop. You’ll also pass by the Hammond Harwood House and the William Paca House, both of which share the central front door, symmetrically aligned windows, and traditional brick facade emblematic of Georgian architecture (Annapolis is known as the “city of brick” and famously has more Georgian-style houses than anywhere else in the United States). Fitting right into this historic pedigree, Annapolis Inn has centuries-old Georgian design roots dating back to the 1770s.
With Annapolis surrounded by water on three sides, you’ll have plenty of beautiful harbor views from your window as you go by City Dock, watching sailboats coast along scenic Spa Creek. As the center of Annapolis’ storied maritime heritage, passing along the boat-lined marina at City Dock is a memorable portion of the trolley route, and it may even inspire you to take a guided Annapolis water tour on a different day during your stay.
During one of many highlights of the tour, your trolley guide will take you across the Naval Academy Bridge to the Maryland WWII Memorial, which recently celebrated its 25th anniversary. Vertical columns surround an outdoor amphitheater and represent the 48 states during WWII that sent troops into battle. Interspersed throughout are granite slabs inscribed with the names of over 6,400 Marylanders who died during the war, a solemn reminder of their sacrifice. Appropriately, the trolley then stops at the overlook adjacent to the memorial, with stunning views of the Severn River and the United States Naval Academy, where today’s brightest and boldest serve our nation.
Planning Your Trolley Tour Around Other Annapolis Events
The Discover Annapolis yearly trolley schedule coincides with the First Sunday Arts Festival, which takes place from May through November on the first Sunday of every month. The Annapolis Visitor Center (where the trolley tour starts and ends) is right in the center of the arts fest action on West Street, perfect for checking out the 100+ arts vendors and live music after your tour. Upcoming 2024 First Sunday dates are October 6th and November 3rd, the last fest of the year, which features a unique holiday market, ideal for doing some early Christmas shopping while enjoying live outdoor performances from the Ballet Theatre of Maryland.
Fill out your Annapolis visit by planning your trolley tour on the same weekend as a USNA home football game or the massively popular sailboat and powerboat shows during the first two weeks of October. Enjoy the 10 am or 12 pm trolley tour, returning just in time to see the midshipmen march in uniform and formation from the USNA campus through downtown to the Navy-Marine Corps Memorial Stadium, a college gameday experience unlike any other and steeped in tradition. The Annapolis Boat Shows have been going on since 1970 and attract thousands of visitors, so book your trolley tour soon for those weekends, as they will likely sell out quickly.
Stay with us and see Annapolis from a unique perspective aboard a trolley tour!