These 6 Towns In Delaware Have The Best Main Streets

Delaware is not always the first place travelers consider, yet its history runs deep. It was the first state to ratify the U.S. Constitution in 1787, and long before that, the Lenape and Nanticoke peoples lived throughout the region. Dutch settlement shaped its early towns, many of which still show traces of those eras in brick streets, small museums, and preserved landmarks. Across the state, these communities often center around walkable Main Streets that reveal how much of Delaware’s past remains part of daily life.

Lewes

Lewes’s downtown centers on Second Street, the town’s primary shopping and dining corridor. Visitors find shops, restaurants, and several historic sites throughout this area and the surrounding streets. Many of the buildings feature traditional brick facades that highlight the town’s long architectural history. St. Peter’s Episcopal Church, located nearby, features mid-19th-century Gothic Revival architecture, one of the notable historic styles present in Lewes. Another significant landmark in the district is the Governor Ebe W. Tunnell House, once the home of Delaware Governor Ebe W. Tunnell.

Just off Main Street, the Zwaanendael Museum on 102 Kings Highway presents the town’s maritime history. Lewes also has small cafes, including The Coffee Mill, known for its calm setting. After time downtown, visitors can head to nearby natural areas such as Cape Henlopen State Park. The park’s dunes, marshes, and beaches give a clear sense of the region’s landscape.

Georgetown

Georgetown’s Main Street centers on The Circle, a busy hub with a fountain, a small park, and brick buildings that reflect the town’s history. Walking around the area gives a clear view of its older structures and quiet small town atmosphere. The park’s open space adds a calm spot to sit or have a simple picnic.

Several cultural sites sit near this part of town. The Marvel Carriage Museum highlights local history through antique carriages and related exhibits. Nearby, the Georgetown Historical Society presents stories from the community through its collections. For a meal, Bella Capri Restaurant & Grill serves Italian dishes, including pasta. Georgetown also has access to green spaces beyond downtown. Trap Pond State Park, in the wider region, draws visitors for hiking among cypress trees and kayaking on calm ponds.

Milford

Milford is known for its scenery along the Mispillon River. Main Street spans North and South Walnut Street, both shaped by this riverfront setting. On North Walnut Street, visitors find community sites such as the Milford Museum, which presents the town’s history, and the Mispillion Art League gallery, which hosts rotating exhibits and art workshops.

South Walnut Street has several cafes and restaurants. For a quiet afternoon, River Lights Cafe offers a calm riverside setting and reliable coffee. Another option is La Hacienda, which serves both coffee and Mexican dishes. Milford’s Main Street also supports community events throughout the year. The Riverwalk Freedom Festival draws visitors to the riverfront, while the Bug & Bud Festival remains one of the town’s most recognized seasonal gatherings.

Rehoboth Beach

Rehoboth Beach is a busy coastal town known for its sandy shoreline and boardwalk along the Atlantic. In summer, the town fills with visitors from cities such as Washington and Baltimore. The center of activity is Rehoboth Avenue, the town’s Main Street, where shops, restaurants, and local attractions line the road.

Dining options include Grotto Pizza, known for putting cheese on first and sauce on top. Frank & Louie’s Italian Deli is another well-known spot, recognized for its buttercake. For ice cream, The Ice Cream Shop on Main Street has more than 100 flavors. During the summer months, Rehoboth Avenue hosts the town’s farmers market, a place to find local produce and handmade goods. Shops range from boutiques to small gift stores, including the Black Dog General Store, which offers a variety of clothing and other items.

New Castle

Walking along New Castle’s Main Street, also called Delaware Street, gives a clear view of historic buildings, small shops, and local eateries. The brick structures reflect the town’s early history and set a steady tone for the area. One of the most noted sites on the street is the New Castle Court House Museum, which outlines the town’s past and the role this spot played when Delaware separated from Pennsylvania in 1776.

Another historic site is the Amstel House, where visitors can follow the life of Governor Nicholas Van Dyke during the Revolutionary War era. New Castle’s Main Street also sits close to several outdoor spaces. Battery Park, along the Delaware River, offers a quiet stretch for a short walk and open views of the water.

Newark

Newark’s Main Street is a bustling community hub with shops, cafes, and restaurants. More than 60 businesses line the street, offering visitors numerous options to explore. One long-standing stop is Bing’s Bakery, considered Delaware’s longest-running bakery. Originally called Fader’s Bakery, it opened in 1871 and continues to serve a steady range of baked goods.

After a pastry, visitors can see several historic sites on Main Street. Deer Park Tavern has ties to the Revolutionary War period, and the Pencader Heritage Museum presents local history through its exhibits. With the University of Delaware nearby, Main Street stays active with students and community events.

For time outdoors, Newark has several parks and trails beyond the downtown area. The James F. Hall Trail offers a quiet route through the woods, while the Newark Reservoir provides an open path for a walk with views of the surrounding landscape.

Visiting Delaware

The historic character and steady activity of these Main Streets show why they stand out within Delaware. Each town reflects a different part of the state’s past, from the preserved streets of New Castle to the coastal setting of Rehoboth Beach. Walking through these areas offers a direct look at local history and community life. These streets also create clear starting points for short visits and road trips across the region, with museums, small shops, and nearby parks shaping much of the experience.