The Best Small Towns In Delaware To Chill Out In 2024
Being the second-smallest state in the US, Delaware is often overshadowed by states with bigger city attractions. But for those looking to chill out in 2024, Delaware’s smaller crowds make it the perfect place to unwind and disconnect from the stresses of everyday life. Whether savoring the region’s beaches or exploring the historic small towns this “First State” is famous for, Delaware invites its visitors to experience a more mellow side of the country.
However, do not mistake laid-back for boring. With tons to see and do, including a wide range of festivals celebrating Delaware’s vibrant heritage, seasons, and holidays, this historic state has something exciting for everyone. From art festivals to beer festivals and everything in between, Delawareans know how to have fun and chill out. With that being said, here are 7 of the best Delaware towns to do just that.
Lewes
Located at Cape Henlopen, where the Delaware Bay converges with the Atlantic, Lewes is a charming historic town blending history and coastal beauty. As Delaware’s first European settlement, the past is entwined with the town’s festivities, like their annual History Book Festival happening September 27th, 2024 and the Historic Lewes Farmers Market on October 5th. That same day, Lewes will also celebrate its famous coastal scenes and maritime past with their 28th annual Boast the Coast festival.
Also celebrating the beauty that drew settlers here so long ago, attractions like the Cannonball House Maritime Museum are a year-round delight. On the other hand, features like the Zwaanendael Museum and historic downtown attest to the town’s remarkable preservation. Even Cape Henlopen State Park commemorates Lewes’ vibrant past, with rumors of pirate treasure buried here by famous pirate Captain Kidd. But the park’s true treasure is its 6 miles of serene beaches, making swimming, windsurfing, and hiking just a few ways to enjoy Lewes’ subtropical climate and gorgeous coastal views.
Rehoboth Beach
Less than a half-hour drive from Lewes, Rehoboth Beach is another beautiful Atlantic Coast town with tons to see and do. Branded the “Nation’s Summer Capital,” classic beach days are a staple of this seaside town. The mile-long Rehoboth Beach Boardwalk features an eclectic mix of family-friendly beach attractions and restaurants like the Funland amusement park, Obie’s By The Sea, and Starkey's Ice Cream. But of course, the adjacent beach is the real star of the show, with plenty of warm sand and sunshine to go around.
Summertime in Rehoboth Beach may be the most popular time to visit, but the fun does not end there. Autumn in Rehoboth Beach brings its own excitement, with plenty of events that keep people coming even when the weather cools. September 14th, 2024 is when the town will host the Indian River Marina Autumn Art Festival, and October has tons of events on the agenda as well, including the Rehoboth Beach Jazz Festival, Schellville Fall Harvest Fest, Sea Witch Festival, and Southern Delaware Food and Wine Festival.
Bethany Beach
For those looking to chill in the sand and enjoy a less crowded boardwalk, nearby Bethany Beach is a wonderful alternative as one of Delaware's “Quiet Resorts.” While the town’s beach is wide and invites its fair share of beachgoers in the summertime, the adjacent half-mile boardwalk is less flashy than Rehoboth’s and offers more peaceful ocean views. What it lacks in bustling amusement parks, it replaces with charming beachside eateries, shops, and attractions like the Turtle Beach Cafe, Turtle Moon Designs, and Bethany Beach Bandstand for live music.
September 7, 2024, will also host the town’s 46th Annual Bethany Beach Boardwalk Arts Festival. Featuring over 100 artists and vendors, including jewelry makers, woodworkers, painters, and more, the festival is a fun way to support local artists and get some early holiday shopping done. The event will also feature a wine-tasting addition, with over 60 wines to try at the Harvest Tide Steakhouse venue.
Milton
As we wave goodbye to summer in the months ahead, Milton is an adorable town to embrace the changing seasons. Located on the scenic Broadkill River, the connecting Delaware Bay is home to natural attractions like the Prime Hook National Wildlife Refuge. Protecting over 10,000 acres of wildlife habitat, the refuge is the perfect place to witness the area’s seasonal foliage and reconnect with nature. Whether driving past the marshes or strolling any of the 7.5 miles of hiking trails, the blissful views are well worth the trip.
As a historic shipbuilding town and former “Holly Capital of the World,” fall and winter are some of the best times to experience Historic Milton. While the shipyards are long gone, the Milton Historic District is charmingly frozen in the 19th century, visible in buildings like the Milton Historical Society Museum, originally built in 1857. Following October events like the Punkin Ale Fest and Wags and Whiskers Fall Festival, Milton also hosts its annual Holly Festival in December to celebrate the town’s history and heritage.
Milford
Perched on the scenic shores of the Mispillion River, Milford is a laid-back river town perfect for those seeking a slow pace and small-town vibe. As the star attraction, the Mispillion weaves through the heart of Milford’s downtown, providing picturesque views for every stroll. From the Mispillion Riverwalk, visitors are opened to a world of different scenes and experiences, including fairytale bridges, cute shops like Lady Maggie’s Boutique, and cafes like Dolce Bakery and Coffee Shop.
From May through October, the Riverwalk Farmers Market is another delight, offering a special Fall Market in November. Bear in mind that autumn in Milford can be on the busier side since the river’s surrounding foliage transforms with the season in a really stunning way. As for events, in September, Milford also hosts the annual Riverwalk Freedom Festival with vendors, food, and fireworks displays. But no matter the season, the nearby Riverfront Theater is highly recommended for year-round live entertainment.
New Castle
Situated on the Delaware River, New Castle is another picturesque river community with a cozy small-town feel. Infused with a history spanning centuries, this former state capital is a charming retreat from the nearby city of Wilmington, inviting visitors to slow down and appreciate life’s simple pleasures. Visitors can stroll the cobblestone roads for riverside views or step back in time to explore New Castle’s impressive range of museums, including the 18th-century historic Amstel House, Old Library Museum, New Castle Court House Museum, Dutch House Museum, and more.
For history lovers and beer enthusiasts, the New Castle Historic Penn Farm will host the 2024 Belgian Beer Fest on September 28th, featuring newly imported Belgian Beers that have never been sampled on US soil. But if you miss the date, Jessop’s Tavern is a fun alternative. Featuring a unique dining and drinking experience commemorating the town’s colonial history, Jessop’s is an absolute must to get the full Historic New Castle experience. The restaurant features servers in period costumes, colonial-inspired dishes, and a broad beer selection.
Newark
Finally, we have Newark, a haven for Delawareans who love to chill out in nature. Home to Rittenhouse Park and White Clay Creek State Park, picnics and hikes are a thing of beauty in this green space town. The first of the 2 boasts 46 acres of woodlands and almost 2 miles of easygoing hiking trails, while White Clay Creek State Park features a more broad range of experiences. Highlights include 37 miles of trails, a 200-year-old home, which is now a Nature Center, and Clay Creek, a National Wild and Scenic River. Famous for its fish-filled waters, anglers come from near and far to try their luck at the river, while nature lovers and hikers find the creek-side trails equally heavenly.
Back in town, Newark offers an even wider range of activities for people of all ages. Whether hunting for treasures at Aunt Margaret's Antique Mall, taking an art class at Painting with a Twist, or catching a concert at the Bob Carpenter Center arena, fun is around every corner. For those marking their calendars, late September 2024 is also when Newark hosts its annual Delaware Saengerbund Oktoberfest, and a few months later, Winterfest takes place in December.
Final Thoughts
Delaware may be small, but its attractions are mighty. Whether dreaming of a classic beach and boardwalk experience at Rehoboth Beach or craving a quieter day of museum-hopping in New Castle, there is something for everyone in this “Small Wonder” state. And for those marking their calendars for the months ahead, exciting festivities await in these 7 Delaware towns. From Lewes’ coastal festival to Milton’s celebration of fall, chilling out in Delaware has never been better.
