Tired of living in the big city? As its intimate size might suggest, Delaware is home to many historic small towns perfect for putting down roots. Whether you’re looking for a safe place to raise a family, you’re tired of the hustle and bustle of city living, or you’re entering retirement and looking for a welcoming neighborhood community, Delaware’s many charming towns are sure to satisfy your desire for a simpler lifestyle.
Lewes
With a population of 2,961, Lewes makes just about every list of best places to live and the best small towns in Delaware, and with good reason. Lewes is known as the first town in the first state and is naturally home to many historic buildings. Interesting spots like the Zwaanendael Museum, ocean-front resorts, and beautiful recreational areas like Cape Henlopen State Park make Lewes a popular vacation destination, but it’s no less popular with residents lucky enough to live there year-round.
Favorite nearby restaurants for locals are Agave (Mexican), Matt’s Fish Camp Lewes (seafood), Crooked Hammock Brewery (beer and new American), and Heirloom (new American).
Rehoboth Beach
Just on the other side of Cape Henlopen State Park and just a few minutes away from the above-mentioned Lewes, is Rehoboth Beach. With a population of 1,218, Rehoboth Beach is quite possibly Delaware’s most popular vacation town but also has both highly-rated public schools and holds the number 1 spot for the best place to retire in Delaware. Beyond its pristine, scenic beaches, Rehoboth Beach is full of fun bars, coffee shops, restaurants, and shopping outlets like Tanger Outlet Center, The Shops at Rehoboth Mewes, and Penny Lane Mall. Great shopping and zero sales tax? Sounds like a match made in heaven.
Favorite nearby restaurants for locals are Shorebreak Lodge (new American, seafood, cocktail bar), Stingray (Sushi Bar + Asian), BlueCoast Seafood Grill and Raw Bar (seafood), and The Fork and Flask (new American, cocktail bar, Asian fusion).
Bethany Beach
Down the coast from Rehoboth and Lewes is Bethany Beach, which has a population of 1,010. Residents love to stroll down the wide boardwalk, which follows the coastline. With Delaware Seashore State Park to the north and Fenwick Island State Park to the south, Bethany Beach is a shining example of how Delaware residents prioritize an active outdoor lifestyle. This town has a laid-back vibe, to which its movies on the beach, free concerts, golf clubs, and surf shops certainly contribute.
Favorite nearby restaurants for locals are Off the Hook (seafood, cocktail bar, desserts), Bethany Boathouse (bar, seafood, sandwiches), and The Cottage Cafe (traditional American, seafood, bar).
Hockessin
Westhampton has officially SOLD OUT as of September 2021 but a beautiful new and exciting community is coming to Hockessin soon.
Introducing: Valley Grove. Learn all about this new community and sign up for the interest list to receive the latest news and updates at the community logo above!
With a population of 13,672, Hockessin is one of Delaware’s slightly larger small towns. Hockessin is a suburb of Philadelphia and therefore a popular home base for many professionals who need to commute to the city for work but want to enjoy small-town living. It’s also just twenty minutes from Wilmington, the largest city in Delaware, so bigger city amenities are within easy driving distance. Communities like Westhampton, a luxury town and twin home community just two miles outside Hockessin, combine the best of small-town living and big-city amenities. Ranked number 3 in best suburbs to live in Delaware, Hockessin is also home to many retirees.
Favorite nearby restaurants for locals are The House of William and Merry (new American), Lettie’s Kitchen (traditional American comfort food), and Mexican Table (Mexican sports bar).
Milton
Milton, DE has a population of 2,792. Milton houses nearly 200 registered historic buildings, but even with these gems, its median home prices and rent prices are affordable. Beer enthusiasts will be happy to hear that Milton is also home to the Dogfish Head Brewery, which is famous throughout the States. A popular town for both young professionals and retirees, Milton offers recreational activities like kayaking, fishing, and golfing. It’s also home to fun festivals like the Horseshoe Crab & Shorebird Festival, the Broadkill Banjos & Seafood Festival, and the Holly Festival.
Favorite nearby restaurants for locals are Tequila Real Mexican Grill (Mexican), Po'Boys Creole Restaurant (Cajun/Creole, seafood), and The Suburban Farmhouse (cafe, breakfast, and brunch, sandwiches).
Millsboro
Millsboro has a population of 4,181. Called one of the prettiest towns in southern Delaware, Millsboro is a growing and thriving town and even ranked number 1 out of all 25 Sussex County cities for the number of residential building permits issued. Given that Sussex County is Delaware’s fastest-growing county, this number is especially impressive. Since crimes are low and beaches are just 20 minutes away, this city is popular with young professionals and families.
Favorite nearby restaurants for locals are Bluewater Grill (traditional and new American, steakhouse), Plate & Palette (gastropub), and Country Kitchen (new American, Italian, comfort food).
Old New Castle
With a population of 5,364, historic Old New Castle offers affordable housing and is popular with young professionals and retirees alike. New Castle is just 10 minutes south of Wilmington, Delaware’s largest city. This town also enjoys easy access to major interstate highways like I-95 and I-295, and it’s located on the beautiful banks of the Delaware River. History buffs will love the fact that New Castle is the second most important Colonial/Federal village in America (Williamsburg, Virginia being the first) in terms of the historic structures’ number and authenticity.
Favorite nearby restaurants for locals are Jessop’s Tavern (traditional American pub), Nora Lee’s (Cajun/Creole), and Ioannoni’s Bullroasters (sandwiches).
Odessa
With a tiny population of 601, Odessa is a truly intimate town. But its small size is no reflection of the importance of its landmarks. Many of its buildings from the colonial era have made it a National Registry District, and the Corbit-Sharp House is a National Historic Landmark. As one might expect, Odessa is home to a number of fascinating antique collections, period room settings, and quaint exhibits. Its streets alone are worth walking and it is located just minutes from great neighborhoods.
Favorite nearby restaurants for locals are Cantwell’s Tavern (a gastropub and bar also serving breakfast and brunch), Uncle Tony’s Kitchen (Italian), and The Hearth Restaurant (traditional American cuisine).
Wyoming
With a population of 1,554, Wyoming has been ranked Kent County’s second-best place to live. Its public schools are highly rated, its housing and rent are affordable, and many families and young professionals live here. With all these great traits, it’s no surprise that Wyoming, DE made the Delaware 2019 Home Snacks list of top ten best small towns to live in. From the idyllic Fifer Orchards to the fun-filled Brecknock Park to the historic Johnson Victrola Museum, there’s no shortage of fascinating small-town charm in Wyoming.
Favorite nearby restaurants for locals are Restaurant 55 (traditional American food), Cheddar’s Scratch Kitchen (American comfort food), and Cool Springs Fish Bar and Restaurant (seafood).
