8 Friendliest Towns to Visit in Delaware in 2024

Between booking accommodations and finding the best sights and activities for your next trip, you often don’t think about the friendliness of your destination. The reality is that, no matter how Instagram-worthy a must-visit travel destination is, if the locals are cold and unwelcoming, your trip will surely be tainted. Even a simple gesture, like pointing you to the right street or having a nice quick conversation with a local, can mean a lot during a vacation.

Delaware might not be as big or visited as its nearby states like New York and Pennsylvania, but its small-town culture, charming locales, and friendly vibes should be on your radar for future trips. Read on to discover the nine friendliest towns to visit in Delaware in 2024!

Lewes

Both big in historic charm and friendliness, sail away to the seaport town of Lewes and experience its Dutch and nautical heritage and warm hospitality. Despite being a small town with only 3,000 people, it hosts events year-round, like its annual Cottage Tour, where locals showcase their historic houses, its free summer concerts at Stango Park, and its weekend Historic Lewes Farmers Market.

The Zwaanendael Museum, a charming museum built to honor the town’s first European settlement, often has events that share Dutch history and folklore. This town often has themed events fit for the season, like a mermaid-focused event for the summer. Those big on boats will love how welcoming the town is with its docking facilities—a mere walking distance from restos, boutiques, and lodgings. After a day at Lewes, enjoy fish and chips during Happy Hour with the locals at Irish Eyes Pub!

Milton

With nice views of the Broadkill River, within close proximity to Delaware Bay, and its shipyard heritage, Milton is a quaint historic town that will charm your socks off with its views, riveting history, and welcoming locals. It is reported as one of the safest cities in Delaware in 2024, too!

Locals recommend kayaking and fishing on Broadkill River or hiking at Edward H. McCabe Nature Preserve for outdoorsy visitors. If you are into history, they will be glad to have you at their yearly architecture walks with the Milton Historical Society. If you are ever in the mood to party, time your visits so you can catch their annual Horseshoe Crab & Shorebird Festival, where they celebrate Milton’s wildlife and local eats.

Wyoming

If you love peaches and a community that is warm and hospitable, book your next summer vacation in Wyoming, Delaware. Visitors mainly flock to this small town for its Wyoming Peach Festival, an annual celebration of Wyoming’s thriving orchards and strong love for peaches. Get a tour of the town’s biggest orchard, enjoy homemade peach ice cream lovingly made by the locals, check out over 200 vendors and crafters, and be amazed at the local’s sweet-tooth creativity at their Peach Dessert Contest.

But there is more to Wyoming than peaches. You can hike, jog, and fish at the beautiful Wyoming Lake and Wyoming Park. Live your rustic farm dreams and pick fresh berries and flowers at Fifer's Orchards. With how peach-sweet this town is, it’s easy to see why it’s called “The Best Little Town in Delaware”.

Millsboro

If you want to take it easy on your next Delaware vacation, consider the stunning and tranquil town of Millsboro. Cupola Park and Millsboro Pond are great spots for fishing, crabbing, swimming, picnicking, and lazying the day away while enjoying waterfront views. Locals are also happy to share their marina with eager fishers and boaters, and you can conveniently find fishing and pontoon boats for rent at the docks.

If water activities aren’t your jam, the town also has the Nanticoke Indian Museum, where you can learn more about the town’s Indigenous peoples. Other historic spots worth checking out are the Isaac Harmon Farmhouse and the Harmony Church built in 1891.

Bethany Beach

Often regarded as one of Delaware’s best-kept secrets, the tranquil coastal town of Bethany Beach welcomes visitors to enjoy its waters and bustling boardwalk. Before hitting the beach, visit Bethany Surf Shop for surfboards, swimming apparel, and fun commemorative clothing for your vacation. Then, mingle with the locals at the Bethany Boardwalk while you sip refreshments from Mango’s or munch on some baked goods from Maureen’s.

After all that excitement, you can relax and stretch it out through daily sessions with Beach Yoga with Monica. For music lovers, Bethany Beach is jam-packed with music events this 2024, so better schedule your visit during the town’s Seaside Concert Series.

Clayton

Nestled between the counties of New Castle and Kent, Clayton is one of the quaintest, safest, and most peaceful towns to visit in Delaware. Just after Milton, Clayton ranked second in Safewise’s report on the safest Delaware cities, so rest assured you can hike or jog along the town’s cozy Providence Creek without worry.

Want to bag unique items during your stay? Join the monthly auction at Delaware Auction Center or browse the miniature collections of Fingertip Fantasies Dollhouse. After shopping, taste the city’s best eats at Jack’s on Main, built in Clayton’s old 1868 town hall. Don’t pass up on “The Perfect Ten” in their menu, which is a filet mignon with a crab cake!

Fenwick Island

Unlike its bigger and rowdier beach town neighbors, Fenwick Island (along with Bethany Beach) has been dubbed as “The Quiet Resorts” in Delaware. Rich in history, laid-back vibes from the locals, and exciting family-friendly activities, Fenwick Island is an excellent destination for your next family vacation.

Start with a selfie at the Fenwick Island Lighthouse, a monument to the town’s guiding nature since 1859. Then find out how the locals enjoy their never-ending summer at Fenwick Island State Park, Coastal Kayak, and Thunder Lagoon Water Park. Water slides, paddleboarding, go-karting, Viking golf, and lounging at the beach are just some of the activities that await you in this Delaware paradise.

Odessa

Let Odessa whisk you away to a bygone era with its 18th- and 19th-century buildings and love for history. Its residents are proud of their heritage and history preservation, which you will know more about from the Historic Odessa Foundation. History buffs will absolutely fall in love with the Corbit-Sharp House, a perfectly preserved 18th-century abode with intact furnishings and trinkets, whose role in America’s history during a tumultuous time is remembered.

Be sure to visit in September for the town’s annual Historic Odessa Brewfest and watch the town’s residents demonstrate Odessa’s brewing culture during the colonial period. Come in December and watch the town come alive as it transforms its usual historic tours into a Christmas wonderland. To fully immerse yourself in Odessa’s history, stay at the colonial-style house, the Miller-Dunham House Bed and Breakfast, then have tasty grubs with your amber brew at Cantwell’s Tavern.

As travelers, you can’t help but yearn for that genuine human connection while traveling. No matter how much of a must-visit a tourist attraction is, friendliness and warm hospitality will make or break a location’s charm. Luckily, Delaware has got that covered!

Despite being the second smallest state in the United States (second only to Rhode Island), Delaware is overflowing with friendliness, authenticity, and hospitality from its tiny towns. From historic seaports like Lewes and Fenwick Island’s beach getaways to Wyoming’s peach festival and the old tavern in Odessa, these are the friendliest towns to visit in Delaware in 2024. Let the locals show you how happy and proud they are of their small-town wonders!