11 Picture-Perfect Main Streets In Delaware

Delaware’s most captivating main streets reveal centuries-old churches, waterfront boardwalks, and preserved colonial shops. From the colonial brickwork of Delaware Street in New Castle to the beachside bustle of Rehoboth Avenue, these thoroughfares capture the state’s diverse identity in just a few blocks.

Some streets lead straight to the shoreline, like Savannah Road in Lewes, where 17th-century buildings meet modern cafés. Others wind past courthouses, art galleries, and historic taverns that have stood for centuries. No matter the setting, each one pairs architectural detail with small-town atmosphere in a way that feels both timeless and unmistakably Delaware. Find 11 of the state’s most picture-perfect main streets, where history fills the sidewalks, and every turn is worth a second glance.

Lewes

Savannah Road forms the historic spine of Lewes, running across the canal to the beach and lined with centuries-old buildings and independent storefronts. It reflects Lewes’ past as one of Delaware’s first settlements, while still serving as a hub of local activity.

At the heart of it stands the Zwaanendael Museum, built in 1931 in Dutch Revival style to honor its 17th-century origins. Just steps away, the Ryves Holt House, dating back to 1665, is the oldest surviving home in Delaware and now hosts a visitor center. Nearby, the Lewes Historical Society campus includes several restored buildings and walking trails that connect history with daily life. Shops, cafes, and galleries fill the blocks between the canal and the coast, with benches and bike racks inviting slow exploration.

Rehoboth Beach

Rehoboth Avenue in Rehoboth Beach stretches from the highway to the Atlantic, ending at one of the East Coast’s most recognizable boardwalks. It used to be a train route for vacationers in the late 1800s; the street now has local boutiques and beach gear stores that stay lively year-round. A replica of the Cape Henlopen Lighthouse marks the central roundabout, a modern addition that nods to the area's coastal roots.

Just steps from the avenue, Funland has operated since the 1940s, and classic amusement rides are still in use today. The nearby Rehoboth Beach Bandstand hosts free concerts each summer, continuing a tradition that began in 1963. At the opposite end, Dogfish Head Brewing and Eats draws crowds with locally brewed beer and live music.

Milford

North Walnut Street of Milford’s historic main street is framed by 19th-century architecture and enhanced by a thoughtful streetscape. Restored facades, vintage-style lighting, and nature-filled sidewalks give the area a timeless quality without losing its everyday appeal.

Just a block away, the Mispillion Riverwalk runs along the water’s edge, linking downtown to nature trails, boat ramps, and Goat Island Nature Area. The riverbank hosts popular events throughout the year, including summer concerts and the annual Riverwalk Freedom Festival held on the third Saturday of September.

Landmarks like the Parson Thorne Mansion and the Bank House offer a glimpse into Milford’s early years, while nearby galleries, coffee houses, and restaurants keep the street lively.

New Castle

Delaware Street, New Castle, can be found in one of the most intact colonial districts on the East Coast. You will see rowhouses, cobblestone corners, and original 18th-century buildings. At its center stands the 1732 Court House, where Delaware’s first reading of the Declaration of Independence took place and where the state’s unusual circular border was established.

Historic homes like the Amstel House and Dutch House offer guided tours, while the Read House & Gardens showcases Federal architecture and landscaped grounds along the Delaware River. A few steps away, Battery Park stretches along the waterfront with serene walking paths and open green spaces. Cafés and longtime favorites like Jessop’s Tavern keep the street active, while annual events like “A Day in Old New Castle” on the third Saturday in May, bring the past to life with reenactments, colonial crafts, and open-house tours.

Newark

Main Street in Newark blends university life with historic architecture, creating one of Delaware’s most active and visually appealing corridors. Lined with brick storefronts, the street hosts over 80 businesses, from local coffee shops and bookstores to longtime staples like the Deer Park Tavern, a Greek Revival landmark operating since the 1850s.

Historic buildings such as the former Newark Opera House and the Exchange Building add architectural interest, while a walking loop through the Old College Historic District connects the street to the University of Delaware’s oldest campus buildings. Events like the Food & Brew Fest, held on the last Saturday of July, and year-round programming from the Downtown Newark Partnership keep the street energized, balancing its academic setting with a strong sense of community.

Dover

Loockerman Street is the historic and commercial spine of Dover, decorated with early 20th-century stores and anchored by the 1875 Kent County Courthouse. The street connects government buildings with small businesses, offering a clear window into the capital’s civic and cultural life.

Just off the main drag, pocket parks like Loockerman Way Plaza and Mary Street Park offer shaded benches and public art. Shops such as Forney’s Too and local favorites like The Scoop keep foot traffic steady with collectibles, sweets, and a family-friendly atmosphere. The street also hosts key events like Dover Days, on the first weekend in May, where parades, vendors, and historical reenactments spill into the surrounding Green.

Milton

Union Street is in Milton’s historic district, where nearly 200 preserved structures reflect architectural styles from the Federal period to late Victorian. The Lydia B. Cannon Museum, housed in a 1859 former church, and the Milton Theatre, opened in 1910, highlight the area’s cultural past. Nearby, the Hazzard and Ponder houses connect the street to early state leadership.

Just off Union, the Broadkill River provides public access for kayaking and fishing, while nature preserves like McCabe and Pemberton offer walking trails through woodlands and wetlands. Union Street also hosts seasonal farmers' markets and summer events that keep the area active year-round.

Smyrna

Main Street and Commerce Street sit at the center of Smyrna’s downtown, where 18th- and 19th-century buildings reflect its early civic life and evolving identity. Landmarks like the Smyrna Museum Complex, housed in the former Barracks building, and the restored Smyrna Opera House offer direct connections to the area’s past and remain active parts of the community today.

Just off the main street, the historic Belmont Hall, an 18th-century Georgian mansion tied to early Delaware leadership, anchor walking tours that highlight Smyrna’s architectural variety. The Henry Levin Center preserves antique pharmacy tools and ephemera inside a once-working drugstore, adding a niche layer of local history.

Seasonal events like Smyrna at Night held early summer in June, bring energy to the streetscape, while nearby breweries and cafés fill visitors with local joy and plenty to drink.

Georgetown

The Circle is the defining feature of Georgetown, a perfectly round public square established in 1791, surrounded by historic buildings that continue to serve as civic landmarks. At its center stands the Sussex County Courthouse, a Greek Revival structure completed in the 1840s, anchoring the city both geographically and historically.

Around the perimeter, sites like the Old Sussex County Courthouse, the 1836 Brick Hotel, and the Richards Mansion reflect a blend of architectural styles, from Georgian to Second Empire. Many of these structures are still in use today as offices, museums, or heritage spaces, preserving their function along with their form. Georgetown’s most distinctive tradition, Return Day, takes place right on the Circle every two years on the Thursday following Election Day, where political rivals symbolically bury the hatchet in front of a public crowd. With its symmetry, preserved character, and ceremonial role in Delaware history, the Circle offers a main street experience unlike any other in the state.

Odessa

Main Street in Odessa is a showcase of early American architecture, where preserved 18th- and 19th-century buildings can be found in the village’s historic district. The Corbit-Sharp House, built around 1774, stands as a National Historic Landmark, and nearby structures like the 1855 Odessa Bank and a collection of restored homes reflect Georgian, Federal, and Italianate styles.

Across the street, Cantwell’s Tavern continues to serve guests in the same 1822 building that once welcomed ship captains and travelers. The Historic Houses of Odessa offer guided tours through five preserved properties, including one that contains a documented hiding space used along the Underground Railroad. Events like the Odessa Brewfest, held annually on the first Saturday after Labor Day, and Christmas in Odessa, held on the first Saturday in December, bring life to the street throughout the year, while shaded sidewalks make it a rewarding walk in any season.

Delaware City

Clinton Street is at the core of Delaware City's historic district, with 19th-century clapboard buildings guiding you toward Battery Park at the riverfront. Established in the 1820s alongside the Chesapeake & Delaware Canal, the area boasts over 200 preserved structures showcasing Greek Revival and Italianate styles.

Battery Park stretches along the water, complete with benches under mature trees and views of passing freighters, canal locks, and distant Fort Delaware. Nearby, a former canal worker’s home now serves as the Historic District Center, offering exhibits on the canal’s impact on city life. Each September and October, Clinton Street comes alive during Canal Fest and Delaware City Day. These events feature boat parades, artisan vendors, live music, and fireworks by the waterfront.

Delaware’s most striking main streets aren’t always the busiest, but they leave a lasting impression through their design, history, and daily rhythm. From the coastal charm of Savannah Road in Lewes to the canal-facing blocks of Clinton Street in Delaware City, each corridor reflects its community’s roots while staying relevant in the present.

These streets balance preservation with local life. They are scenic and functional spaces that continue to evolve, host events, and bring people together. For anyone seeking a closer look at Delaware beyond the highway exits, these main streets are the perfect place to start.