Trolley Square, Wilmington

Trolley Square is one of Wilmington’s most dynamic and walkable neighborhoods, combining historical charm with modern urban energy. Originally developed in the 1860s as the city’s trolley system pushed into farmland once owned by the Shallcross and Lovering families, the area takes its name from the former trolley depot and bus barn that once operated here. Although those original structures were demolished in the 1970s, the space was transformed into a shopping complex that opened in 1978, ushering in a new era for the neighborhood.

Today, Trolley Square is a tightly knit community bordered by Harrison Street, Pennsylvania Avenue, Lovering Avenue, and the CSX railroad tracks. At its core is The Village-an adaptive reuse of the former depot that now hosts over 80 galleries, restaurants, and shops. This commercial and cultural hub offers tax-free shopping and a vibrant mix of offerings, from casual seafood eateries with fresh raw bars to boutique stores and cozy coffee spots. Live entertainment and a fun, friendly atmosphere make it a favorite destination for both locals and visitors.

Despite its urban density, Trolley Square retains a strong neighborhood feel. Its compact layout and pedestrian-friendly streets attract a wide mix of residents-from young professionals to families and retirees-who enjoy its charm, accessibility, and community spirit. The area’s highly rated public schools and liberal, engaged population add to its appeal as one of the best places to live in Delaware.

Whether stopping in for fresh oysters and live music or browsing the diverse storefronts and galleries, Trolley Square offers a blend of historic roots and contemporary culture. It’s a place where the past and present comfortably intersect, and where Wilmington’s character shines through.