9 Best Towns In Delaware For A Two-Day Recharge
Delaware, situated on the Delmarva Peninsula’s northeastern portion in the Mid-Atlantic region of the United States, and oftentimes left unnoted in place of its neighboring states, has, with time, evolved into one of the Eastern Seaboard’s best-loved getaway destinations. The "First State's" heterogeneous terrain, ranging from the undulating hills of the Piedmont region to the damp marshes of Delaware Bay and sandy beaches of the Atlantic, is peppered with the populous Wilmington and the capital city, Dover. Numerous quintessential towns guarantee weekenders an optimal balance of recreation and relaxation on their two-day escapes.
Smyrna
Constituting a portion of the Dover metropolitan statistical area, Smyrna extends across Central Delaware’s Kent and New Castle counties, just 14 miles north of Dover and 30 miles south of Wilmington. Initially called "Duck Creek Cross Roads" for its setting along Duck Creek, the settlement was retitled for the identically named ancient Greek seaport of Smyrna in modern-day Turkey. Holidaymakers on a tour to this prominent agrarian, transportation, and light industrial hub must check out the numerous old properties, such as the Cummins-Stockley House, filling the 132-acre Smyrna Historic District; take note of The Plank House and The Barracks at the Duck Creek Historical Society-owned Smyrna Museum Complex; partake in recreational activities at the Big Oak County Park; and stay at the Quality Inn.
Hockessin
A picturesque settlement on the eastern banks of Mill Creek in New Castle County, Hockessin, named after the Lenape word hokes, meaning "good bark," is located within 1.2 miles of the state boundary between Delaware and Pennsylvania. This community invites travelers to explore the many long-established buildings, such as the Trinity Community Church and the nearby Marshall Steam Museum & Friends of Auburn Heights, where you can observe the world’s biggest functioning collection of Stanley steam cars. Hang out with kith and kin amidst the tranquil, beautifully maintained Swift greens, and engage in wildlife-watching activities and enjoy your stay at an overnight lodge at the Ashland Nature Center.
New Castle
Originally settled as "Fort Casimir" in 1651 by the Dutch West India Company and renamed "New Castle" by the English in 1664, New Castle sits six miles south of Wilmington in New Castle County. Whilst stopping over in New Castle, stroll through the cobblestone streets of the New Castle Historic District, which has well-looked-after heritage structures such as the Amstel House, the Immanuel Episcopal Church on the Green (the state and the country’s oldest Anglican parish), and the New Castle Court House Museum (also part of the First State National Historical Park), deemed to be one of nation’s ancientest courthouses. Have a good time hiking the 3.7-mile-long paved trail at Battery Park, please your palate with signature New Orleans-inspired gastronomies at Nora Lee’s French Quarter Bistro, and make yourself at home in Fairfield Inn & Suites Wilmington New Castle.
Millsboro
Located just a half-hour drive from Bethany Beach, this welcoming community along the Indian River in Sussex County seamlessly fuses small-town prettiness with state-of-the-art conveniences. A utopian haven for environmental zealots, Millsboro provides hassle-free access to adventurists wanting to take part in copious water-based activities like boating, fishing, swimming, crabbing, etc. In the downtown area, you can shop for antiques at Black Cat Antiques and for economical merchandise at Blooming Boutique. Savor traditional Mexican dishes at La Tonalteca Millsboro. Ease off at the budget-friendly Atlantic Inn, Millsboro, post bird-watching, fishing, and picnicking at the Cupola Park.
Odessa
This peaceful paradise by the Appoquinimink River in New Castle County, initially christened "Cantwell's Bridge" and renamed in the 19th century for the Ukrainian port city of Odessa, is widely known for its mind-boggling past and small-town enchantments. History mavens on a tour to this only 366-inhabitant town can catch sight of the age-old Appoquinimink Friends Meetinghouse, the Old St. Paul’s Methodist Episcopal Church, and abundant other contributing properties in the Odessa Historic District. Participate in various outdoor activities at the Odessa Memorial Park, attend the Historic Odessa Brewfest of the Historic Odessa Foundation (slated to be held on September 6, 2025), and get some sleep after a stressful day at the colonial-style Miller-Dunham House Bed & Breakfast.
Delaware City
Delaware City is a teeny port town in northern Delaware’s New Castle County, situated on the eastern end of the Chesapeake & Delaware Canal. Excursionists holidaying in this bewitching oceanfront community should take a ferry ride to the 248-acre Fort Delaware State Park on the low-elevated marshy Pea Patch Island and direct attention to the iconic Fort Delaware commanding the Delaware River. Aside from this, mark the distinct Greek-Revival- and Italianate-style buildings like the Delaware City Hotel in the Delaware City Historic District; visit the Fort DuPont State Park, which features the home field of the vintage baseball team Diamond State Base Ball Club, apart from proffering opportunities for an array of open-air activities; feast on fresh seafood in Crabby Dick’s restaurant; and rest for the night at Miss Helen’s Guesthouse.
Milton
An alluring Sussex County town, Milton, named in memory of the eminent English poet John Milton, is set along the Broadkill River’s headwaters on the Delmarva Peninsula. Owing to the waterside setting and being part of the speedily prospering Cape Region, the town beatifically endorses its seafaring heritage and small-town magnetism. Encompassing a substantial portion of Milton’s central business district and its adjoining areas, the Milton Historic District includes multiple late-18th to early-20th-century properties like the Lydia B. Cannon Museum Building and Gov. James Ponder House (currently Short Funeral Services Inc.). Watch artistic performances at Milton Theatre, a prime event venue; rub shoulders with families and friends at the Milton Memorial Park; sample specialty beers served by the Dogfish Head Milton Brewery; and snag some z’s at the Mansion Farm Inn bed and breakfast.
Lewes
Called “The First Town in the First State,” Lewes is an enticing coastal community in Sussex County, located where the Delaware Bay and the Atlantic Ocean meet, approximately 117 miles east of Washington, D.C. Placed betwixt the unspoiled beaches of Cape Henlopen State Park and the sweeping coastal marshes of the Great Marsh Preserve, Lewes is overflowing with plentiful architectural treasures, among which the National Register-listed Lewes Presbyterian Church and the Ryves Holt House, purportedly Delaware's oldest surviving house and dating back to 1680, are the most salient. Additionally, uncover the secrets of all those who resided on Delaware’s southeastern coast through the varied exhibits at the Zwaanendael Museum, shop at the Lewes Gifts gift shop, be there at the Lewes Chamber of Commerce’s Annual Boast the Coast Maritime Festival on October 4, 2025, and de-stress at The Blue Water House bed and breakfast.
Bethany Beach
Set on the Atlantic coast and rimmed by the Delaware Seashore State Park to the north, this appealing family-centric beach town in Sussex County is part of the Salisbury, MD-DE Metropolitan Statistical Area. Popularly called "The Quiet Resorts" alongside the neighboring coastal settlements of Fenwick Island and South Bethany, Bethany Beach is renowned for its unobstructed shoreline access, fresh seafood, inexhaustible beachside amusements, and peerless panoramas from the Bethany Beach Boardwalk. Furthermore, take note of the interactive exhibits and the wooded trails that thread through verdant areas at the Bethany Beach Nature Center, see the nearby Fenwick Island Lighthouse (the state’s oldest lighthouse), sample oceanic cuisine and custom-made cocktails at the Bluecoast Seafood Grill & Raw Bar, and unwind at Bethany Beach Ocean Suites Residence Inn.
From the colonial architecture and cobblestone streets of New Castle to the storied past of Lewes, the blissful towns in the nation’s sixth-least populous and second-smallest state woo vacationers with their gorgeousness. Flaunting unpolluted sandy shores, praiseworthy tourist highlights, incredible wilderness areas, high-end stores, upscale diners in the inviting downtowns, comfy accommodations, and affable locals, these unrivaled Delaware towns are perfect for a quick weekend break.
