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13 Charming Small Towns in Delaware

By Emma Singer

| Jul. 18, 2022

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It might be the second smallest state in the country, but Delaware has a ton to offer visitors—particularly if a mellow beach retreat is what you’re after. From quaint riverside villages and coastal communities to historic colonial destinations, here are the most charming small towns in Delaware. Read on and start planning your trip for when the forecast is warm and sunny.

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1. Lewes

Why We Recommend It: beaches, historic, scenic
Where to Stay: 829 Savannah

The oldest town in the first state, Lewes is known for its historic architecture and vibrant energy. Yep, this Delaware community might be small, but the town center—replete with restaurants and boutiques—is far from snoozy. Best of all, Lewes is located between the Great Marsh Preserve and Cape Henlopen State Park, which means you can take a stroll through scenic wetlands or lounge on pristine beaches when you’re done exploring the town.

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2. Milton

Why We Recommend It: shopping, historic, quiet getaway, water activities
Where to Stay: The Charleston of Milton Inn

Located at the mouth of Broadkill River and just a stone’s throw from Delaware Bay, Milton is a picturesque riverside town with plenty to do. Aside from fishing, canoeing and other outdoor activities, Milton also boasts an impressive Historic District where the town’s Victorian past is impeccably preserved. Last but not least, Milton is home to Dogfish Head—a popular craft brewery that can’t be missed if you’re in the mood for a cold one.

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3. Smyrna

Why We Recommend It: galleries, restaurants and breweries, hiking
Where to Stay: Suite Deal Comforts

This Northern Delaware gem, situated on the banks of both Lake Como and Duck Creek, is prized for its natural beauty. Nature lovers can take a scenic hike through Blackbird State Forest, which boasts 5,400 acres of gorgeous woodlands, and observe the incredible avian and wildlife at the nearby Bombay Hook National Wildlife Refuge. If arts and culture is what you seek, be sure to take a tour of the historic artifacts and paintings at the Smyrna Museum and pay a visit to the Smyrna Opera House—a beautifully restored historic venue for the performing arts with an art gallery attached. Plus, Smyrna’s large number of distilleries and microbreweries promise to make happy hour dreams come true.

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4. Laurel

Why We Recommend It: historic, beautiful natural scenery, wildlife, outdoor activities
Where to Stay: Motley Home

Outdoor enthusiasts looking to escape city life will fall in love with Laurel, a small historic town surrounded by breathtaking natural scenery. The town itself is quiet (the population is about 3,000 people), but recreational activities abound—including hiking, biking, wildlife viewing, as well as fishing and kayaking at Broad Creek, or any of the region’s numerous lakes and ponds.

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5. Dewey Beach

Why We Recommend It: quiet beaches, vibrant nightlife, great restaurants
Where to Stay: Beach House Dewey

In case you missed it, Delaware is an ideal destination for a beach vacation—and Dewey Beach is arguably the state’s best-kept secret. Both the ocean and the bay beaches here are immaculate and considerably less crowded than neighboring spots. Don’t be fooled by the calm and peaceful daytime atmosphere, though—this coastal town has plenty going on, and is known for its top-notch waterfront restaurants and vibrant nightlife scene.

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6. Bethany Beach

Why We Recommend It: lots of boutiques, quiet beaches, laid-back vibe
Where to Stay: Steward’s Watch

Here, another option for a quiet beach getaway—this seaside town, a favorite among locals, has an intimate feel that’s just right for a laid-back vacation. Gourmet seafood is always on the menu at the many restaurants in town, and the streets and boardwalk are lined with boutiques where visitors can enjoy tax-free shopping. Plus, if you’re into surfing, you’ll be stoked to learn that Bethany Beach is just a quick drive away from Fenwick Island State Park where you can ride some of the best waves the Delaware coast has to offer.

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7. Fenwick Island

Why We Recommend It: water sports, family friendly
Where to Stay: Sea Harbor Condo

Fenwick Island is an ideal destination for families that serves up a winning combination of outdoor excitement, family-friendly attractions and the beautiful sandy beaches of Fenwick Island State Park. Kids will have a blast playing mini golf, racing go-karts and speeding down water slides at Thunder Lagoon, and there’s ample opportunity for visitors of all ages to enjoy a wide range of water sports.

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8. Millsboro

Why We Recommend It: scenic, close to beaches, shopping
Where to Stay: The Small Easy

Situated along the banks of the Indian River, Millsboro is a quaint riverside town that provides easy access to the neighboring coastal destinations on our list and enough charm to be a suitable home base. When you’re not busy lounging on one of the nearby beaches, carve out some time to explore downtown Millsboro, an eye-pleasing strip that boasts a boatload of boutiques, restaurants and antique shops. The town is also home to Cupola Park—a tree-lined public space on the river where visitors can picnic, fish in the ponds or simply go for a leisurely stroll. Another lovely place to spend the day is the modestly-sized but oh-so idyllic Edward H. McCabe Nature Preserve, where hiking trails weave through both swamp and upland forests and wildlife abounds.

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9. Frederica

Why We Recommend It: natural scenery, good for fishing, laid-back vibes
Where to Stay: Frederica Family Home

Dubbed “Frogtown” because of its proximity to the wetlands, this Kent River County village is a former port town with a quiet, old-timey feel. You’ll find excellent seafood on the wharf of this scenic fishing village and plenty of natural beauty, to boot. If you’re looking for a low-key place to enjoy a serene retreat, Frederica fits the bill.

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10. Hockessin

Why We Recommend It: hiking, natural scenery
Where to Stay: Cozy Cottage

Beloved by nature enthusiasts, the New Castle County town of Hockessin is home to the Ashland Nature Center, which features a truly magical butterfly house, as well as numerous walking trails and birdwatching spots. There’s also Mt. Cuba Center, a fairytale-esque sanctuary with acres of scenic gardens and breathtaking landscaping. And with Wilmington, Maryland just a short drive away, big city attractions are within reach too.

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11. New Castle

Why We Recommend It: historic, quiet, close proximity to a city
Where to Stay: Apartment Wilmington

Attention history buffs: New Castle is the place to visit if you want a colonial education. Not only is this small town chock full of historic homes and gardens, but it also has multiple museums and landmarks—the Old Court House Museum and First State National Historical Park, among others—that are dedicated to Delaware’s rich past. Indeed, despite being mere miles away from the bustling city of Wilmington, a stay in New Castle promises little hubbub and loads of history.

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12. Arden

Why We Recommend It: quirky, historic
Where to Stay: Rustic Getaway

Arden, a tight-knit community of less than 500 people, can be found on the National Register of Historic Places. It’s also pretty offbeat in that village life is shaped by a variety of guilds (or “gilds” as the folks of Arden spell it) that members of the community participate in. The main attraction here is the Labyrinth of the Ardens—a sprawling labyrinth designed by the community to be a meditative space, though if you’re lucky enough to be in town when the Shakespeare Gild performs at their outdoor theater, we highly recommend sticking around for the show.

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13. Rehoboth Beach

Why We Recommend It: family friendly, great shopping and restaurants
Where to Stay: Eagles Landing Retreat

Here, one of the most popular beach destinations in Delaware, and for good reason. Rehoboth Beach is equal parts sophisticated and family friendly, with a famously welcoming laid-back community of locals. Aside from the gentle waves and miles of sandy beach, this spot also has a particularly active boardwalk and town center—both of which feature numerous boutiques, quirky shops and excellent casual dining options, to boot. In other words, when it comes to coastal town destinations, this one checks all the boxes.

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13 Charming Small Towns in Delaware

1. Lewes

2. Milton

3. Smyrna

4. Laurel

5. Dewey Beach

6. Bethany Beach

7. Fenwick Island

8. Millsboro

9. Frederica

10. Hockessin

11. New Castle

12. Arden

13. Rehoboth Beach

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13 Charming Small Towns in Delaware

1. Lewes

2. Milton

3. Smyrna

4. Laurel

5. Dewey Beach

6. Bethany Beach

7. Fenwick Island

8. Millsboro

9. Frederica

10. Hockessin

11. New Castle

12. Arden

13. Rehoboth Beach

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