There are many charming small towns in Delaware and we've found one of the most fun ones. Dewey Beach is one of the best beach towns in Delaware and is only a mile long and two blocks wide, making it one of the tiniest towns in Delaware. Despite its size, it's a fiercely popular town for visitors and Delawareans alike, thanks to its party atmosphere, family-friendly activities, delicious dining scene, and picture-perfect beach. Perhaps it's not one of the more quiet towns in Delaware, but you will enjoy all the fun things to do in Dewey Beach.
Dewey Beach has been a popular vacation spot for decades, though it was only incorporated as a town in 1981!
The population has been growing here year over year, but there are still just under 400 residents. In the summer, it's normal for 30,000 or more tourists to flood the town each weekend.
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Present-day Dewey has turned into one of the coolest towns in the Northeast.
The Bottle & Cork is one of the best music venues in the area, and summertime sees music lovers from all over the state descending upon the town to turn it into a music mecca.
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While Dewey certainly has a party reputation, there are plenty of family-friendly events here all summer long.
These crab cakes are so famous that there are hundreds of them served every day during the busy summer months. Dewey's restaurant scene is well known throughout the state of Delaware for being a balance of perfectly fried bar food and gourmet meals.
Whatever you're looking for in a town, you'll find it in Dewey Beach.
The town's event calendar can fill you in on the busy weekends they plan, including fall festivals for canines and humans alike. This tiny town is even host to the East Coast Skimboarding Championships, so get practicing!
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Dewey Beach is the coolest town in Delaware, for sure, but there are plenty of other small towns in Delaware worth checking out! Tell us in the comments about what you enjoyed about Dewey Beach. While you're staying in this awesome town, here are some more fun things to do in Dewey Beach:
Lewes, Delaware was the first town founded in Delaware. As one of the most charming beach towns in Delaware, Lewes has been one of the state's favorite places and nearly anyone who visits will fall in love! Delaware coastal communities like this one have such a great feel to them. Lewes has one of the best beaches in Delaware and you'll love exploring it.
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Lewes is a small town right at the mouth of the Delaware Bay. It's truly surrounded by natural beauty.
While you browse about town, you'll walk past countless historic buildings. Be sure to find the cannonball from the war of 1812 that's still lodged in the walls of this historic home.
Do you agree that Lewes, Delaware is one of the most charming beach towns in the state? What is your favorite thing about Lewes? Let us know in the comments if you've been here and what it was like for you. If you're staying in Lewes and are looking for even more fun things to do here, we've got you covered:
The eastern coast of the United States is home to countless charming coastal towns, and Lewes, Delaware, is one of our absolute favorites. Nestled along the coast of Delaware between Rehoboth Beach and Ocean City, Maryland, to the south, and Cape May, New Jersey, to the north across the Delaware Bay, Lewes is a dreamy destination for a weekend getaway – especially in the late summer or early fall months. I've visited this tiny community twice now, and each time, I fall more in love with its charming streets, historic buildings, and access to water. I even do that thing where I imagine what it would be like to live in this coastal community – and let me tell you, it's a gorgeous vision. Whether you want to soak up the sun at the beach or simply love immersing yourself in history, Lewes is a must-visit.
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From the coast of Oregon to the mountains of Pennsylvania and everywhere in between, there are countless charming and captivating small towns across America worthy of a weekend getaway. Curated by our team of local travel experts, you’ll love our 2024 Small Town Getaways.
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History Of Lewes
The first European settlement in Delaware, Lewes, was established in 1631 as a whaling and trading post. Lewes is often called “The First Town In The First State” since it was the earliest settlement in the state, and Delaware was the first state to ratify the Constitution.
A year later, in 1632, a group of local inhabitants killed the colony's 32 settlers as a result of a dispute over a Dutch coat of arms the settlers had mounted. That wasn’t the only time the town was settled and abandoned. In 1682, the land was conveyed to William Penn by the English Courts and named Lewes in honor of the town in Sussex County, England.
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Pirates visited Lewes as late as 1698, and a British frigate bombarded the town during the War of 1812. Today, Lewes remains a quintessential seafaring town and East Coast port of call. It is home to a substantial fleet of charter fishing boats and the Delaware Bay and River Pilots Association base. Lewes is also the site of the University of Delaware College of Marine Studies.
In a word, yes. If you’re a fan of seafaring history, coastal architecture, the Atlantic Ocean, quaint shops – especially antique stores – and scrumptious dining, you’ll fall in love with Lewes. No matter what time of year you visit, you’ll find coastal charm around every corner.
How To Get To Lewes
If you live in Maryland, Delaware, or even New Jersey, Lewes is a picturesque destination for a weekend getaway.
You can drive from Wilmington in less than two hours (approximately 90 miles). Whether you drive from Baltimore, Maryland, Philadelphia, Pennsylvania, or Washington D.C., the drive is approximately 120 miles or two to two-and-a-half hours, depending on traffic conditions.
I drove into Lewes from outside of Annapolis, Maryland. As soon as I had made it across the Chesapeake Bay Bridge, I thoroughly enjoyed the drive – it isn’t often near where I live that you get to enjoy the laid-back nature of driving in the country.
You can also visit via the Cape May - Lewes Ferry, a passenger and vehicle ferry that connects Lewes to another equally charming coastal town: Cape May, New Jersey.
While you can drive through Lewes, the downtown area is best experienced on foot. Ample street parking is available, which is metered from May 1 through October 1. Both times I visited – on a November weekend and a summer weekday – I easily found parking. I imagine it might be harder to find parking on summer weekends.
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Once you have secured your parking space, it’s time to start walking. While you might be tempted to throw on your sandals, I recommend solid walking shoes here. While the beach is less than a mile from the downtown area, you’ll likely want to explore separately. I recommend parking downtown to enjoy all of the shopping and dining options available to you in the morning and then driving down to the beach after lunch to soak up the sun and make a splash.
Best Time To Visit Lewes
There is never a bad time to visit Lewes, though the town unsurprisingly comes alive in the summertime.
I’ve visited in both the on and off seasons, and have to say, I prefer summer. Sure, that’s because I will always choose warm over cold weather, but I also feel like this town truly thrives in the sunshine. Yes, there are more visitors, but shops are also more open, and it’s easier to slow down and truly enjoy the simple life.
A boutique hotel nestled in the heart of Lewes, Hotel Rodney was built in 1926 on the corner of Second and Market Streets. The hotel is central to the town's history and charm and is the perfect home base for a weekend spent exploring Lewes and the coast of Delaware.
If you want a little more space or to stay closer to the beach, this Airbnb is as charming as they come. This quaint Airbnb sleeps four individuals in two bedrooms and comes with two complimentary bikes for you to use throughout your stay. The rental has a full kitchen, fenced-in patio, and easy parking – a rarity in downtown Lewes.
Located at 218 Second Street, the Ryves Holt House is purportedly the oldest surviving house in the state of Delaware. Using dendrochronology, the building has been dated to 1665, and serves as one of the earliest inns in the region. The home was purchased by Ryves Holt in 1721, the first Chief Justice of Sussex County. The Ryves Holt House was added to the First State National Historical Society, and today, the building is owned and operated by the Lewes Historical Society.
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When I visited, the staff were friendly and knowledgeable, and I enjoyed chatting with them about the history of the town and what it's like living in such a picturesque location: the tourists who visit in the summer make traffic hard to navigate, but they also enjoy interacting with more people who want to understand this town's great history.
From its construction circa 1740 to 1750, the Cannonball House has witnessed centuries of Lewes history. It is one of the few intact examples of a form prevalent in Lewes during this time: making economic use of an early dwelling while adapting to architectural trends.
The building was used as a home throughout the 1700s and 1800s, when it was hit by a cannonball during the British Bombardment of Lewes in 1813 – hence the name "Cannonball House." The original cannonball is on display within the home, which is now a museum, but also once served as city offices, a printing shop, a laundromat, and the Lewes Service Station.
Managed by the Lewes Historical Society, this district is home to nine historic buildings for visitors to explore, including the Hiram Rodney Burton House (c. 1720, the only building on its original site), the Burton-Ingram House (c. 1785), the Rabbit’s Ferry House (c. 1740), the Thompson Country Store (c. 1800), the Ellegood House and Blacksmith Shop (c. 1790), the Doctor’s Office (c. 1850), and Midway School #178 (c. 1898).
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These museums highlight Lewes's relationship to the sea as well as its dedication to the preservation of history. My favorite was the on-site antique store housed in a historic building. If I thought it could fit in my car, I would have gone home with a furniture piece or two.
The site of a defense battery in 1812 and founded as a park to commemorate the defense of Lewes against a British bombardment in 1813, 1812 Memorial Park is a unique – and picturesque – slice of history. The park is situated along the Lewes-Rehoboth Canal and also serves as the entrance to the Otis Smith City Dock.
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On the upper terrace, you will find four large guns, and on the lower terrace, a three-inch naval gun that was used during World War I and placed here by the American Legion in 1930.
Nestled along the canal in Lewes, Delaware, this family-friendly park is home to a playground, walking paths, and stellar views. The park also regularly hosts outdoor movies, concerts, and plays and features a marina with floating docks, fishing pier, gazebo and arbor, and a boat ramp for kayaks and canoes
During my visit(s) to Lewes, I enjoyed a leisurely stroll through the park, soaking in the sunshine and watching the boats.
The Lightship Overfalls (LV-118) was built in 1938 for the U.S. Lighthouse Service, was decommissioned by the U.S. Coast Guard in 1972, and has been docked in Lewes since 1973. The Lightship LV-118 was renamed Overfalls in honor of the nearby Overfalls Shoals lightship station – and the American lightship sailors that served there. Today, a dedicated team of volunteers preserves, maintains, and operates the historic ship as a museum.
Built and founded in honor of Delaware's first European colony, Swanendael – which was established in 1631 by the Dutch – the Zwaanendael Museum showcases Lewes' maritime, military, and social history.
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I was immediately drawn to the building's architecture, and loved meandering through the nearby park with a smoothie before exploring the small free museum.
If you ask my spouse, I am decidedly not a fan of shopping – but give me a small town full of charming boutiques and a few hours to explore, and I will do some serious damage. I love supporting small businesses, and Lewes is full of them. Some of my favorites are Lewes Lettering Co., Lewes Gourmet, and Puzzles. I also love Biblion, a used bookstore, and Fair Godmother, the cutest baby and toddler clothing shop.
If you’re interested in antiques, Lewes has several phenomenal antique stores, including this charming spot (pictured above), which directly benefits the Lewes Historical Society.
I ordered the Original Agave Margarita – on the rocks, of course, as if there’s any other way – and the soft shell steak tacos, which came with a side of rice and beans and were stuffed with steak bites and tasty vegetables, topped the most mouthwatering chipotle mayo I’ve ever tasted.
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I also have to pat myself on the back for this one: I visited Lewes by myself, and this was the first time dining solo in a proper, sit-down restaurant. I had a good book for company and thoroughly enjoyed myself.
If you're anything like me, you are always on the hunt for your next cup of coffee, and Lewes Bake Shop did not disappoint. This small storefront may not look like much, but my vanilla latte and the pastry I purchased to enjoy later were scrumptious.
Tucked inside a small, historic building in the center of Lewes, Olive & Oats is one of the most charming spots I’ve ever dined. The tiny cafe serves a variety of coffees, smoothies, pastries, and Mediterranean sandwiches, salads, and appetizers.
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During this particular visit, I grabbed a green smoothie to go since I wasn't particularly hungry, but I also loved the cafe's Black Pepper-Crusted Turkey Breast and Gourmet Grilled Cheese.
Part cafe and bakery, part home and garden market – The Station On Kings is located on the outskirts of downtown Lewes but is the perfect place to stop on your way into town for a coffee and sweet treat.
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The flavors offered are truly unmatched: I enjoyed a lavender orange latte with a blueberry almond croissant, both of which might have been some of the best of my life. Their glass patio was positively charming, and while the cafe was busy, especially for a random Friday morning, I could have stayed there for hours enjoying my coffee and book.
Nature In And Around Lewes
The focus on nature in and around Lewes is obviously on the Atlantic Ocean, and the area has several incredible beaches.
Measuring nearly 5,200 acres of pristine beachfront land with six miles of coastline, Cape Henlopen State Park is positively gorgeous. The park's strategic location led to the construction of Fort Miles during World War II, which served as a training and testing area and a federal defensive site both during and after the war.
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The park is home to barrier dunes, coastal beaches, and maritime forests, which are all home to a variety of plant and animal species. Whether you decide to make a splash at Deauville Beach, immerse yourself in the natural world at the Nature Center, hike or bike the Gordons Pond Trail, or explore the historic Fort Miles Historical Area, Cape Henlopen State Park has something for everyone to enjoy.
Located just a half-mile from downtown Lewes, there's no better place to spend an afternoon than Savannah & Johnnie Walker Beaches. Part of the city's park system, these two beaches comprise a 1/3-mile stretch of sand, separated by a dune, with parking available at each beach.
Metered parking is in effect from 9 a.m. to 8 p.m. May 1 through September 30, and lifeguards are on duty from Memorial Day weekend to Labor Day. The beach gets busy during the summer, so you'll want to arrive early if you want to secure a prime spot for the day.
Rehoboth Beach is perhaps more well-known than the beaches in Lewes, but these beaches are all equally gorgeous. The Rehoboth Beach Boardwalk, in particular, is worth a visit. We had the entire beach to ourselves when we visited in November, but I imagine this beach is quite crowded during the summer months.
Have you ever visited the charming historic town of Lewes?
We're already dreaming of our next trip to the coast, but we might visit one of our other incredible Small Town Getaways first.
