12 Most Hospitable Towns In Delaware
Delaware might not be the first state that comes to mind when envisioning captivating destinations. However, it could very well be the type of off-the-beaten-path holiday spot to help you unwind. Delaware is an oft-overlooked seaside destination, straddling the Mid-Atlantic and South-Atlantic regions of the U.S. Although its idyllic location spanning a large chunk of the Delmarva Peninsula is often outshone by Pennsylvania, New Jersey and Maryland, this area is every bit a seaside gem. Boasting pristine beaches and a fair share of enchanting holiday spots where friendliness abounds, here we look at the 12 most hospitable towns in Delaware waiting to win you over.
Rehoboth Beach
Rehoboth Beach is très coastal with all the things you would expect to find in a beach town including a bustling boardwalk, arcades and rides, and miles of pristine Atlantic Ocean coastline along Delaware Seaside State Park. Smiles abound at the charming outdoor Penny Lane Mall located in the heart of town. This is the quintessential seaside shopping experience with sweet little storefronts and welcoming locals selling wares ranging from gifts at Old Salt to ice cream at Archie’s. Satisfy your sweet tooth with a bag of authentic Dolle’s saltwater taffy just steps from the boardwalk where friendly staff have served up this chewy confection since 1927.
Accommodations exude warmth whether you prefer a true boutique experience at the casual, comfy Ocean Glass Inn or long to be spoiled at the luxurious Hotel Rehoboth or Bellmoor Inn and Spa. Dine overlooking the ocean at the very sociable establishment Above the Dunes, enjoy drinks at the gracious Key West inspired Purple Parrot Grill, or indulge in innovative cuisine and cocktails in pleasant company at The Blue Hen.
Milton
Why should seaside towns get all the attention? Milton is always finding new ways to welcome visitors to their charming Delaware town. Although it might not have miles of beaches or stroll-worthy boardwalks, Milton gets brownie points for eclectic events that attract visitors throughout the year. From the Horseshoe Crab Festival in May to the Mead, Metal, and Viking Festival in June, Milton is all about entertaining visitors with new and exciting experiences. This is definitely a town where the quirky and artsy feel welcome, from history lovers immersing themselves in the bygone days of the Vikings to comic book fans spending hours browsing at Ogre’s Grove.
The Off-Centered Tour indulges beer lovers at The Dogfish Head Brewery, while you can encounter the work of yet-to-be-discovered local artists at Milton Arts Guild Gallery. Tequlia Real serves up next level Mexican with the warmth of a long-lost friend, overlooking Wagamons Pond. Rest your weary head at the Old-South inspired Charleston of Milton Inn after a day of exploring.
Lewes
Lewes is brimming with seaside town hospitality, making it a wonderful place to spend a day or week relaxing and taking in coastal life. Quirky boutique hotels help raise the bar with welcoming accommodations close to popular destinations including Delaware Bay Beach and Cape Henlopen State Park. They each offer their own twist of friendliness with Hotel Blue winning out for warmth and whimsy, and Hotel Rodney taking the prize for old-school charm in a high-end 1920’s restoration.
However, Dogfish Inn, located on the Lewes-Rehoboth Canal, takes whimsy to a whole new level. Its contemporary beach town vibe is clearly all about casual, comfortable fun. Dogfish Alehouse extends the warm feels tenfold, where locals and visitors rub elbows dining on scratch-made fare. A town steeped in history, nine historic sites take you back in time, complete with welcoming historians in vintage costumes ready to answer your questions and share stories about the town’s heralded maritime past.
Laurel
Laurel is located almost smack dab in the middle of the Delmarva Peninsula on the banks of Broad Creek not far from the meandering Nanticoke River. This town focuses its own brand of first-class hospitality on its proud history. The Old Christ Church built in 1772 sits beside Chipman’s Pond. As one of the few remaining wooden structures of its kind in America, you can picture gatherings with locals sitting shoulder to shoulder in pre-Revolutionary wooden box pews under an impressive barrel-vaulted ceiling.
The highlight for history lovers is the Laurel Heritage Museum, located in the old Laurel Train Station. It offers a rare glimpse at town life dating back to 1898 and spanning the first half of the twentieth century, captured by local photographer, Albert Waller. The Dutch Country Market offers authentic Pennsylvania Dutch foods served by Amish community members from nearby Dover. The ideal spot for lunch, you will feel like a member of the family, with heaping helpings of comfort food sure to warm the cockles of your heart.
Fenwick Island
This narrow strip of land is flanked by the sparkling Assawoman Bay to the west and the Atlantic Ocean to the east for a double dose of coastal warmth. Everywhere you go you are greeted by smiling faces happy to welcome you to their island paradise.
Beachcombers and sunworshippers dot the quiet shores and waters of Fenwick Island State Park relaxing on tranquil sands, basking in the warm sun, or enjoying the day paddle boating, sailing, or kayaking. Every visit ends with breathtaking views of the setting sun on the uncrowded shores of Assawoman Bay. The park’s dunes are also a favourite spot for companionable surf fishing while the beaches and boardwalk invite people to relish the grand views by foot or on horseback.
After a day enjoying the great outdoors, feed your soul with Catch 54’s coastal cuisine overlooking the bay. Attentive servers greet you like old friends, serving up platters of their signature crab cakes and fresh buttermilk fried oysters. Take advantage of the many vacation rentals available for cozy accommodations hosted by local families happy to share their waterfront or beach views.
Smyrna
At first glance, Smyrna is an unassuming town located near the Northernmost tip of the peninsula. However, as you discover its many quiet attractions, you will also encounter locals who are passionate about their history and the low-key experiences they offer.
Start your day at Helen’s Famous Sausage House, where homemade scrapple and sausage is served with homestyle breakfasts just like mom used to make. From the serene beaches of Lake Como to camping at Blackbird State Forest, Smyrna is blessed with uncompromised beauty. The monthly bird walk is a perfect example of the town’s sociability. Anyone can join the gang gathered in the parking lot at Bombay Hook National Wildlife Refuge Visitor’s Center on the third or fourth Saturday of each month. The roughly two-hour chummy hike along the Forest Discovery Tree Trail is all about sharing nature’s wonders.
Innovative spaces made for mingling with locals over drinks include Painted Stave Distilling, housed in a vintage 1940s movie theater. Known for their unique pairing events ranging from donuts to bread, creative bartenders compatibly match tempting carbs with trademark house cocktails.
Milford
You can judge a town’s hospitality by its event calendar. Milford’s annual Bug and Bud Festival is a cheerful local Arbor Day Weekend event, saluting the town’s designation as a USA Tree City and their state insect the ladybug. The parade features locals dressed in nature-inspired costumes and bicycles adorned with spring decorations, followed by live music, the leisurely sampling of food truck fare, and discovering local finds from craft vendors.
Milford's annual Riverwalk Freedom Festival is held along the picturesque Mispillion River Walk while the toe-tapping Ladybug Music Festival celebrates Women in Music. Milford’s B&B’s continue the Colonial-era custom of welcoming travelers into the home. The historic Towers Bed and Breakfast Inn offers luxury accommodations in rooms restored to their original glory. Their gourmet breakfast is the hallmark of first-class Delaware hospitality.
Causey Mansion is steeped in old-world charm. An enchanting cobblestone path leads to its cheerful yellow façade, surrounded by lovely gardens. Lavish rooms feature snug antique furnishings, and your stay includes a home-cooked breakfast.
Dover
As the capital of Delaware, you would expect Dover to be a highly populated, thriving metropolis. It is not. Instead, it is a picturesque small city centered around the historic public square, Dover Green. The green is the heart of the town, featuring lovely historic brick buildings overlooking a lush, manicured lawn dotted with park benches and tall, shady trees.
While history sets the tone for the capital, interacting with locals in period costumes highlights the sociable feel of the town. As the first state to officially join the Union, Dover’s historic sites, like The John Dickinson Plantation and Old State House, provide honest depictions of life in the early days of Dover. There is a sincere desire to welcome visitors and share insights into the town's history, including more recent stories shared at the Air Mobility Command and Johnson Victrola Museums.
Dover also welcomes birders who “flock” to local parks, including Silver Lake, Fork Branch Nature Preserve Loop and Raymond Pool Loop Trail, to observe the many migratory species passing through the area in the spring and fall.
Yorklyn
Just a tiny dot on the map at the Delaware-Pennsylvania border, Yorklyn is best known for Auburn Valley State Park. Sitting on Red Clay Creek, the park is the former estate of the wealthy Marshall family. Special guided tours take you through the immaculate rooms of their former Queen-Anne style home, while the estate grounds, trails, and Marshall Steam Museum invite visitors to explore.
The family-owned and operated Dew Point Brewing Company’s tasting room and brewery is housed in the repurposed Yorklyn’s historic Garrett Snuff Mill built in 1901. The family greets guests with a selection of craft beers enjoyed overlooking an expansive green space, made all the better on Fridays when food trucks serve up local fare.
Treat yourself to a stay at The Inn at Montchanin Village & Spa, nestled in Brandywine Valley, in nearby historic Wilmington. Guest rooms and suites feature period-appropriate furniture and unique luxuries such as lavish marble baths, private courtyards, or cozy fireplaces. You will enjoy first-class hospitality in a village of carefully restored buildings dating back to 1799.
Ashland
Located just south of the Delaware-Pennsylvania border, Ashland is too far from the ocean to attract crowds of tourists, and just off the beaten path enough to be considered a proverbial “hidden gem.” The Ashland Nature Center Red Clay Scenic Byway is the idyllic road trip to take in the beauty of the area. Stunning old-growth forests, pastoral scenery, and the charming historic Ashland Covered Bridge spanning Red Clay Creek all add to the experience.
While road trips are quite solitary, you will encounter plenty of friendly faces on your journey. Stop at Coverdale Farm Preserve to sample fresh, seasonal produce, or locally owned Woodside Farm Creamery for a scoop of decadent ice cream. Get a quick botany lesson from local experts at Mt. Cuba Center and indulge in a gourmand experience at the House of William & Merry, a refurbished farmhouse just a few miles from Ashland Nature Center.
Delaware City
Everything about Delaware City seems to focus on building a welcoming community. This riverfront town on the banks of the Delaware River maintains a constant drumbeat of events designed to bring people together.
From live music in Battery Park in the summer to the craft show in October, the Delaware City town-wide yard sale held in April, and the Annual Delaware Charity Car Show in the fall, the city welcomes visitors to take part in its events with open arms. There really is something for everyone, making it a great event calendar to keep on your radar.
A ferry ride to Pea Patch Island to visit Fort Delaware State Park could be the highlight of this day excursion. Visitors immerse themselves in living history, helping gracious interpreters dressed in period costumes perform various tasks typical of day-to-day life at the 1864 fort
Middletown
Located near the Maryland-Delaware border, Middletown boasts three local microbreweries ideal for a self-guided brewery tour. As a self-described “brewy utopia,” the Crooked Hammock feels like your closest friend’s backyard with the smell of burgers wafting across the patio and cold brews being served over friendly conversation. You can choose to sit back and relax or get up and join in a game of bocce ball, cornhole or horseshoes.
Not to be “out-back yarded,” Volunteer Brewing Company is literally a backyard beer garden in a renovated formal residence dating back to 1830. Their taphouse is a popular watering hole where people gather to chat over craft beers like guests at a neighborhood party. At JAKL Beerworks, you can switch gears, sipping local beers overlooking the expansive green space of a working farm. Friends since middle school, the owners shared a vision to create a microbrewery and taproom to serve as a community gathering space ideal for friends to meet up for a local brew or attend one of their many local events.
Whether you are a history buff, sun worshipper, nature lover, or brew pub aficionado, the state of Delaware is a veritable getaway haven offering unique experiences with something sure to satisfy your wanderlust.
From short day trips to full-on vacations, you can while away your downtime taking in the warmth and heartfelt experiences that await you at America’s second smallest state. Discover the hospitality of quirky boutique hotels, feel like a member of the family at seaside restaurants, immerse yourself in live history, and create one-of-a-kind experiences unique to the undeniably hospitable towns of Delaware.
