Delaware often flies under the radar when it comes to travel destinations, overshadowed by its more well-known neighbors like Pennsylvania and Maryland.
Yet, those who take the time to explore this small but incredibly charming state are met with an unexpected array of delightful towns, each with its own unique character, rich history, and warm, welcoming atmosphere.
I’ve always been fascinated by places that offer something more than just the usual tourist attractions—towns where history seeps into the very streets, and the people you meet are as much a part of the experience as the landmarks themselves.
Join me as we uncover 12 of the most charming small towns in Delaware, where every corner holds a piece of the past, and every visit promises new memories to cherish.
1. Middletown
Living in Delaware | Lifestyle, Housing, & Events
| Category | Details |
|---|---|
| Location | Central Delaware |
| Population | Around 22,000 residents |
| Known for | Arts community, festivals, and small-town charm |
| Best Time to Visit | Spring and summer for local events and warmer weather |
Middletown is one of those places where the energy of the community fills the streets, making it hard not to love. It’s a small town that thrives on its artistic and cultural spirit, and it shows, especially during its annual Peach Festival and Peach Festival Parade. The town has a wonderful blend of Victorian architecture and modern touches, giving it a timeless feel that’s perfect for a stroll.
The Everett Theatre is one of the top places to visit, where you can enjoy everything from live performances to classic films. The town’s historic district is another must-see, with its charming shops and quaint cafes.
Where to Stay in Middletown
For a comfortable and convenient stay, Motel 6 Middletown, offering affordable prices and easy access to local attractions, is a solid choice.
Where to Eat in Middletown
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If you’re in the mood for a casual meal, Tom Foolery’s Restaurant and Bar is among the best restaurants in this town. Known for its hearty American dishes and lively atmosphere, it’s a perfect spot for lunch or dinner. For something a little more upscale, head to The Middletown Grille, where you can enjoy delicious steaks, seafood, and a great selection of craft beers.
Middletown is one of those hidden gems that is full of surprises, whether you’re walking through its picturesque streets or enjoying one of its local events. It’s a great spot to slow down, soak in the local culture, and enjoy the simpler things in life.
2. Lewes
| Category | Details |
|---|---|
| Location | Southern Delaware, along the Atlantic Coast |
| Population | Around 3,000 residents |
| Known for | Historic harbor, beautiful beaches, outdoor activities, and charming downtown |
| Best Time to Visit | Spring and summer, for pleasant weather and beach activities |
Lewes is a peaceful town with a history that goes back to the 1600s. It’s the kind of place where the past feels present, yet it doesn’t overwhelm. Start with Canalfront Park, where you can watch boats drift by while taking a walk along the canal.
Cape Henlopen State Park is a must-see, offering miles of unspoiled shoreline perfect for beach lovers. Whether you enjoy sailing or fishing, the harbor provides endless ways to explore the area.
The historic Zwaanendael Museum tells the story of Delaware’s Dutch heritage, providing an educational yet laid-back stop for visitors.
Where to Stay in Lewes
For a comfortable, waterfront experience, Hyatt House Lewes Rehoboth Beach is a solid choice. It’s got all the basics—free parking, Wi-Fi, a pool, and a fitness center. It’s also close to downtown Lewes, making it easy to explore the area.
If you’re looking for something smaller and more quaint, The Inn at Canal Square Bed and Breakfast is right by the water, with charming rooms and a peaceful vibe that’s perfect for a weekend getaway.
Where to Eat in Lewes
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When it comes to food, Lewes doesn’t disappoint. Nectar is a great place for breakfast, offering classics like French toast topped with fresh blueberries and ice cream—perfect for those who need a hearty start to their day.
For a casual, cozy dinner, The Rose and Crown gastropub serves up delicious crab cakes, fried green tomatoes, and an excellent selection of beers.
For a more upscale experience, head to The Back Porch Café for fresh, local seafood in a relaxed setting.
3. Dover
| Category | Details |
|---|---|
| Location | Central Delaware |
| Population | Around 38,000 residents |
| Known for | Historical landmarks, museums, and the state’s capital city |
| Best Time to Visit | Year-round, with spring and fall offering mild temperatures |
As the capital of Delaware, Dover is packed with history and culture. A visit to Legislative Hall is a must if you want to see the heart of Delaware’s government and take in some local history.
The Biggs Museum of American Art is another highlight, offering exhibits that focus on local artists and Delaware’s role in the broader American story.
History buffs will also enjoy exploring the Johnson Victrola Museum, which tells the tale of one of the pioneers of recorded sound.
Take a walk through First State Heritage Park for a real taste of Dover’s colonial past, where you can see reenactments and visit historic homes.
Where to Stay in Dover
If you’re in Dover and want to stay in a comfortable, well-located place, Hilton Garden Inn Dover has all the essentials—free Wi-Fi, a pool, and a fitness center. Plus, it’s located close to many of Dover’s top attractions, so you won’t waste any time getting to where you want to go.
If you’re looking for a more budget-friendly option, Microtel Inn & Suites by Wyndham Dover offers free breakfast, parking, and easy access to downtown.
Where to Eat in Dover
Dover has a variety of food options, whether you’re craving something casual or a more refined dining experience. The Greene Turtle is perfect for a laid-back meal with a local vibe, serving burgers, sandwiches, and a great selection of beers.
For a taste of local seafood, head to Dover Downs Hotel & Casino, where you can enjoy some fresh crab cakes or a delicious bowl of clam chowder. If you’re in the mood for something different, Vincenzo’s Pizzeria offers a cozy atmosphere and classic Italian dishes like pasta and lasagna.
4. Rehoboth Beach
| Category | Details |
|---|---|
| Location | Eastern Sussex County, Delaware |
| Population | Around 1,500 residents |
| Known for | Beautiful beaches, boardwalk, and vibrant summer activities |
| Best Time to Visit | Summer for beach activities, or the off-season for a quieter experience |
Rehoboth Beach is Delaware’s most popular beach town for a reason. The Rehoboth Beach Boardwalk is lined with shops, eateries, and arcades—great for a stroll while taking in the ocean view.
Funland offers classic carnival rides and games that will bring out your inner child. If you’re into nature, make sure to visit Cape Henlopen State Park where you can hike, bike, or just relax by the beach. Whether you’re into sunbathing, surfing, or just people-watching, there’s plenty to do.
Where to Stay in Rehoboth Beach
For a comfortable stay right by the beach, Avenue Inn & Spa is a great option, offering free breakfast, a pool, and spa services.
If you’re looking for a more budget-friendly spot, Hotel Wave Rehoboth Beach provides a solid base for your visit with amenities like a fitness center, free Wi-Fi, and a relaxed, friendly atmosphere.
Where to Eat in Rehoboth Beach
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For great seafood, you can’t go wrong with The Cultured Pearl, which offers sushi and classic seafood dishes with a fantastic view of the town. Dogfish Head Brewings & Eats is the place for craft beer and a casual bite—try their wood-grilled pizza or burgers.
For dessert, head to Kaisy’s Delights for some incredible ice cream and homemade waffle cones.
5. Milford
| Category | Details |
|---|---|
| Location | Southern Delaware, near Mispillion River |
| Population | Around 10,000 residents |
| Known for | Outdoor activities, historical sites, and quaint downtown |
| Best Time to Visit | Spring and fall, when the weather is ideal for outdoor adventures |
Milford may be small, but it’s packed with attractions for nature lovers and history buffs alike. Take a walk along the Mispillion Riverwalk or hike through Mispillion River State Park. If you’re interested in history, check out the Milford Museum for a deeper look at the town’s past.
Prime Hook National Wildlife Refuge is perfect for birdwatching, where you can see a variety of species in their natural habitat. Milford’s downtown area is charming, with local shops and cozy cafes to explore.
Where to Stay in Milford
For a convenient and affordable stay, Microtel Inn & Suites by Wyndham Milford offers free breakfast, Wi-Fi, and easy access to the town’s attractions. It’s a practical choice if you’re looking for a simple, no-frills experience.
Alternatively, if you prefer something a bit more personalized, consider staying at The Hotel Rehoboth in the nearby area for a more boutique experience.
Where to Eat in Milford
When it comes to dining, Po Boys Creole & Fresh Seafood serves up delicious New Orleans-style dishes like jambalaya, crawfish tails, and Bayou shrimp. For a casual bite, The Brick Room offers American fare and a cozy, relaxed atmosphere.
Don’t miss Abbott’s Grill, known for its farm-to-table dishes and a great selection of local beers.
6. Bethany Beach
| Category | Details |
|---|---|
| Location | Eastern Sussex County, near the Atlantic Ocean |
| Population | Around 1,000 residents |
| Known for | Quiet beaches, boardwalk, and outdoor activities |
| Best Time to Visit | Summer for the beach or fall for a peaceful retreat |
Bethany Beach is all about relaxation. The beach is quieter than Rehoboth, offering a more peaceful experience with less crowds. Spend your day lounging on the shore or take a stroll down Bethany Beach Boardwalk.
If you’re an outdoor enthusiast, visit Holts Landing State Park where you can fish, hike, or spot local wildlife like ospreys and herons. South Bethany Beach is also a great spot for quieter beach days.
Where to Stay in Bethany Beach
Addy Sea offers a lovely, adults-only retreat with beach access and a serene atmosphere. It’s perfect for couples looking to escape and unwind.
For something more family-oriented, The Bethany Beach Ocean Suites Residence Inn provides spacious rooms and a range of amenities, including a pool and fitness center, making it ideal for longer stays.
Where to Eat in Bethany Beach
The Cottage Café is a local favorite for breakfast and lunch, offering tasty dishes like crab cakes, omelets, and fresh salads. For dinner, head to The Blue Crab for a true seafood experience with an emphasis on fresh, local catches.
If you’re in the mood for pizza, DiFebo’s offers Italian-American classics in a cozy, welcoming atmosphere.
7. Georgetown
| Category | Details |
|---|---|
| Location | Central Delaware, near the Sussex County Fairgrounds |
| Population | Around 7,000 residents |
| Known for | Victorian architecture, local festivals, and the Georgetown Speedway |
| Best Time to Visit | Spring for festivals or fall for the cooler weather |
Georgetown is a small town with a big personality. It’s known for its well-preserved Victorian architecture, which gives the town a charming feel. One of the top spots to visit is the Nutter Marvel Carriage Museum, home to a fantastic collection of horse-drawn carriages.
If you’re in town during the summer, check out the Georgetown Speedway for some exciting local racing. The town also hosts various festivals, including The Georgetown Christmas Parade and The Peach Festival.
Where to Stay in Georgetown
Microtel Inn & Suites by Wyndham Georgetown offers basic amenities, including free breakfast, a pool, and a fitness center. It’s a budget-friendly option that gives you easy access to the town’s attractions.
Where to Eat in Georgetown
For a taste of local flavor, try La Tonalteca, a popular Mexican restaurant known for its flavorful nachos, quesadillas, and margaritas.
For dessert, stop by The Sweet Tooth for homemade ice cream and other treats.
8. Fenwick Island
| Category | Details |
|---|---|
| Location | Coastal town, near the Maryland-Delaware border |
| Population | Around 1,500 residents |
| Known for | Quiet beaches, peaceful atmosphere, and outdoor activities |
| Best Time to Visit | Summer for the beach, or fall for fewer crowds |
Fenwick Island is all about relaxation and outdoor fun. The town’s Fenwick Island State Park offers a quiet place to enjoy the beach, with fewer crowds than neighboring towns. If you’re into water activities, try kayaking or surf fishing in the area.
For some local culture, stop by Fenwick Island Lighthouse, a historic lighthouse that provides sweeping views of the surrounding area. It’s perfect for a peaceful getaway, offering a perfect balance of nature and leisure.
Where to Stay in Fenwick Island
Fenwick Shores, Tapestry Collection by Hilton is a fantastic option for those seeking a peaceful retreat, offering beach access, a pool, and bike rentals. It’s a comfortable choice for families or couples looking to relax while staying close to the beach.
For a more budget-friendly option, Holiday Inn Express & Suites is nearby, offering great amenities like free breakfast, a fitness center, and proximity to local attractions.
Where to Eat in Fenwick Island
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Catch 54 is a must-try for seafood lovers, offering fresh, local dishes like clam strips, crab cakes, and lobster rolls. For a more laid-back, casual dining experience, check out Harpoon Hanna’s, a local favorite with great seafood and waterfront views.
If you’re looking for something different, Crab Cake Factory serves up fresh crab cakes and other seafood dishes that are both delicious and affordable.
9. Dewey Beach
| Category | Details |
|---|---|
| Location | Eastern Sussex County, next to Rehoboth Beach |
| Population | Around 300 residents |
| Known for | Laid-back beach vibes, vibrant nightlife, and live music |
| Best Time to Visit | Summer for the beach and nightlife, or fall for a quieter experience |
Dewey Beach is all about having fun in a relaxed, less crowded setting. The beach is perfect for lounging, swimming, or playing beach volleyball. If you’re looking for a bit of nightlife, Dewey Beach’s bars and clubs are known for live music and great atmospheres.
Rehoboth Bay is a great spot for kayaking, paddleboarding, and even jet skiing. For a change of pace, you can also visit the nearby Indian River Inlet, known for its beautiful views and fishing opportunities.
Where to Stay in Dewey Beach
Hyatt Place Dewey Beach is a great option for families or anyone looking for a comfortable and affordable place to stay. With free breakfast, a pool, and easy access to the beach, it’s a solid choice for a fun vacation.
For something closer to the nightlife and town, The Beach House Dewey is a boutique hotel that’s just steps away from the beach and all the action.
Where to Eat in Dewey Beach
For a casual, tasty meal, The Starboard is known for its crab cakes, cocktails, and relaxed atmosphere.
If you’re in the mood for a burger and fries, Dewey Beer Company offers a fun atmosphere with craft beer and pub-style food.
10. Milton
| Category | Details |
|---|---|
| Location | Southern Delaware, near Prime Hook National Wildlife Refuge |
| Population | Around 2,500 residents |
| Known for | Historic sites, nature reserves, and charming downtown |
| Best Time to Visit | Spring and fall, when the weather is great for outdoor activities |
Milton is a quiet, historic town with plenty to see and do. If you’re into history, check out the Milton Historical Society to learn more about the town’s past. For a peaceful walk, visit Prime Hook National Wildlife Refuge, a 10,000-acre reserve that’s perfect for birdwatching and hiking.
If you’re into shopping, Milton’s downtown area offers unique local shops and charming architecture. Don’t forget to take a look at Milton Theatre, which has live performances and movie screenings throughout the year.
Where to Stay in Milton
Home2 Suites by Hilton Lewes Rehoboth Beach is just a short drive away and offers all the comforts you need—free breakfast, a pool, and a gym. It’s a great option for those looking for an affordable yet comfortable stay.
Where to Eat in Milton
For a great meal in Milton, Po Boys Creole & Fresh Seafood offers excellent New Orleans-inspired dishes like crawfish tails, jambalaya, and shrimp.
11. Odessa
| Category | Details |
|---|---|
| Location | Southern Delaware, near Blackbird Creek |
| Population | Around 400 residents |
| Known for | Historic landmarks, colonial architecture, and scenic parks |
| Best Time to Visit | Spring and fall for pleasant weather and exploring outdoors |
Odessa is small but filled with history. The Corbit Sharp House is a standout, offering a glimpse into the town’s colonial past. The Liston Range Front Lighthouse is another historical landmark worth checking out.
Nature lovers will enjoy the nearby Augustine Wildlife Area and Blackbird Creek Reserve, where you can hike and explore local wildlife in peaceful surroundings. The town’s scenic parks are perfect for a quiet stroll, and the Historic Odessa Foundation Museum is a must-visit for history enthusiasts.
Where to Stay in Odessa
While Odessa is small, nearby towns offer great accommodations. The Inn at Canal Square in Lewes provides a charming, waterfront stay, just a short drive from Odessa.
For something closer, consider The Brick Hotel in Georgetown, offering a boutique stay with easy access to the town’s attractions.
Where to Eat in Odessa
If you’re visiting Odessa, you’ll want to check out The Millstone Café, which offers delicious home-cooked meals in a cozy setting.
The Odessa Diner is a local favorite for a casual meal, serving comfort food and American classics.
FAQs
1. Are there any local festivals or events in Delaware?
Yes, Delaware hosts several local festivals and events throughout the year. Georgetown has the Peach Festival and Christmas Parade, while Dover celebrates with events like Dover Days Festival. Rehoboth Beach also has annual events like the Sea Witch Festival in the fall.
2. Is Delaware a good place for a weekend getaway?
Absolutely! With its small-town charm, beautiful beaches, and rich history, Delaware makes for a perfect weekend getaway. You can explore historic towns like Lewes and Milton, or relax on the beaches of Bethany Beach and Rehoboth Beach.
3. What are the most scenic places to visit in Delaware?
For scenic views, Cape Henlopen State Park offers beautiful beaches and hiking trails. Fenwick Island State Park is perfect for quiet beaches and fishing. Prime Hook National Wildlife Refuge is a great spot for birdwatching, while Lewes offers lovely harbor views.
4. Are there any good places to shop in Delaware?
Yes, Rehoboth Beach is known for its shopping scene, offering everything from boutique stores to larger outlets. Milton has charming local shops, and Georgetown offers antique stores and specialty shops perfect for finding unique items.
5. Can you visit Delaware’s parks in winter?
Yes, many of Delaware’s parks, such as Cape Henlopen State Park and Fenwick Island State Park, are open year-round. While some activities like swimming might not be available, winter visits offer peaceful trails for hiking, birdwatching, and stunning winter landscapes.
Final Thoughts
Delaware is a state that offers something for everyone. Its small towns, full of history, charm, and natural beauty, might not be as widely recognized as some other destinations, but they’ve got plenty to show for themselves.
From the peaceful streets of Lewes to the historic spots in Dover, there’s no shortage of reasons to visit. With quiet beaches, interesting museums, and local favorites to enjoy, Delaware provides a laid-back yet enriching experience that you won’t find elsewhere. If you’re looking for a relaxing getaway, this is definitely a place worth considering.