tigersonthego

By Sebastian Garcia-Dominguez

On a spring evening, my friends and I navigated the bustling weekend traffic of Annapolis to find a spot in the Hillman Garage, open 24 hours a day. Walking out into the evening air, the first thing you notice is the rhythmic clack-clack of tires over the historic brick roads. We headed toward the docks, where the sky transitioned into deep oranges and purples during the sunset. The sight of sailboats bobbing in the harbor provided a peaceful contrast to the lively crowds.

Everywhere you go you feel the history.

The City’s History

Established in 1649 by Puritan exiles from the Province of Virginia, the original settlers named this coastal refuge Providence. The site underwent several name changes, later renamed Town at Proctor’s and then Town at the Severn, before eventually becoming Anne Arundel’s Towne. This title honored Lady Anne Arundell, the late wife of Cecilius Calvert, the second Lord Baltimore.

Today Annapolis offers a vibrant, long history that is presented through its preserved architecture and maritime vibe. Visitors can feel the rough texture of centuries old red brick buildings and smell the briny, salt-heavy air drifting. The sight of the sun reflecting the Maryland State House dome provides a stunning reminder of the city’s enduring legacy.

The heart of this history remains at the Maryland State House, the oldest state capital in continuous legislative use. Standing atop State Circle, the building’s massive wooden dome, constructed without a single iron nail, dominates the skyline. Visitors can feel the gravity of the past while standing in the same room where George Washington resigned his commission as commander in chief of the Continental Army.

Walking alongside the gaslit streetlights of the brick-lined road, we arrived at one of downtown Annapolis’s most famous restaurants: Chick & Ruth’s Delly, situated at 165 Main St. a local favorite since 1965, the deli serves everything from hearty breakfasts to their famous crab cakes. Their walls are covered with photos of the few who managed to complete the daunting 6-pound milkshake challenge.

For dessert, the city offers several options within walking distance. A local favorite is Storm Bros. Ice Cream Factory, located at 130 Dock St. this family-owned business has served customers since 1976, making it a staple of the city’s waterfront community for over four decades. Whether you are seeking a historic landmark or a quiet moment by the harbor, Annapolis remains a masterclass in American preservation and local flavor.