6 Charming Main Streets in Delaware

From bustling main streets to quaint historic strips, here are some walkable roads in Delaware with shopping, dining and entertainment.

A recent survey of 3,000 respondents revealed the nation’s top 100 charming main streets. Newark’s Main Street made the list at 99, and Loockerman Street in Dover placed 86.

Delaware is home to many historic towns and neighborhoods, which means charming main streets aplenty. While the hip college town and historic state capital showed up on the top 100 list, there are many others to explore. Here are a few of our favorite bustling strips, quaint historic streets and more in the First State.

Main Street, Newark

With historic charm, college bars, international cuisine and cute boutiques, Main Street is an ideal destination in Newark. University of Delaware creates a great atmosphere for bars with great food like Klondike Kate’s and Home Grown Cafe. If the college bar isn’t your scene, upscale options like Hamilton’s on Main, Taverna or Caffe Gelato are ideal spots to grab a bite. If you’re looking for international options, Ramen Kumamoto is a local favorite for authentic ramen and Ali Baba is great for Middle Eastern food. For brunch, The Peach Blossom Eatery provides an upscale diner feel with top-notch breakfast, lunch coffee and cocktails.

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Speaking of coffee, Brew HaHa! and Bing’s Bake & Brew are great options for java. Little Goat Coffee Roasting Co. is just off the main strip with top-notch coffee, matcha and more. The Delaware Growler is an ideal place to sample and purchase unique craft beers. Boutiques like Rooted on Main and Bloom are fun for shopping. If you’re into tabletop games, board games, cards, puzzles and more then stop into Days of Knights, a hobbyist shopping hotspot. For entertainment, catch a movie on Main Street Movies 5 or live music at Klondike Kate’s, Grain or Deer Park Tavern.

Loockerman Street, Dover

A walk down Loockerman Street puts you face-to-face with plenty of interesting Delaware and United States history. Just a block away are The Old State House, First State Heritage Park, Legislative Mall and more. The Biggs Museum of American Art is a must-visit for art enthusiasts and casual observers alike. The House of Coffi provides a great cup of coffee. Grab a bite at La Hacienda or Simaron Pizza & Steak and stroll along the historic streets of Dover.

Delaware Street, New Castle

Starting with historic buildings and top-notch eateries and ending with a pier and riverfront views, this strip of Historic New Castle is a must-visit. Plenty of history can be found at the New Castle Court House Museum, the Amstel House, Read House & Gardens and more. For entertainment, catch a jazz act at Zollie’s Jazz Cucina on the weekends. For beer lovers, Jessop’s Tavern is a must-visit with an extensive list of imported and domestic options. Or stop by for old-fashioned ice cream before your stroll through the streets of Old New Castle.

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Main Street, Odessa

Another charming historic Main Street can be found in Odessa. Stop by the new Corner Grounds Cafe before taking a stroll down Main Street. The Historic Odessa Foundation provides tours of the historic Corbit Sharp House. Grab a bite cross the street at Cantwell’s Tavern—a restored 19th-century tavern serving elevated American fare.

Savannah Road, Lewes

Lewes is filled with coastal charm from historic streets and buildings to incredible dining and a small beach. Along Savannah Road, find the Lewes Historical Society Antique Shop and the Zwaanendael Museum. Built in commemoration of Delaware’s first European colony, the Zwaanendael Museum showcases the region’s maritime, military and social history in a Dutch-style building.

Lewes is a dining hotspot with great dining up and down Savannah Road. Raas is a must for Indian food. Just around the corner is Lewes Oyster House, an upscale oyster house serving seafood and raw bar favorites. Heirloom is a local favorite for farm- and ocean-to-table food with a charming historic atmosphere. For an overnight stay, the Dogfish Inn can serve as a great home-base to explore Delaware’s coastal communities.

Rehoboth Avenue, Rehoboth Beach

For the ultimate coastal vibes, head to Rehoboth Avenue in Rehoboth Beach. It’s hard to beat the dining on this Delaware main strip. The Cultured Pearl is a Japanese and sushi spot with an impressive rooftop koi pond among the tables to enjoy a scenic and delicious meal. Lupo Italian Kitchen and Fins Ale House are side by side for upscale Italian food or great seafood and bar fare. Enjoy boardwalk favorites like Thrasher’s Fries and Kohr Bros frozen custard.

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There’s also plenty of boardwalk shopping to enjoy. Veer off down the Penny Lane Mall for gift shops and a great atmosphere. Pink Leopard is great for unique and eye-catching women’s fashion. Browseabout Books is a must-visit for avid readers. For entertainment, the Rehoboth Beach Bandstand hosts plenty of live performances throughout the summer.

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