9 Prettiest Small Towns In Delaware
Delaware's beauty comes primarily from its natural charm. In Lewes, Cape Henlopen State Park offers ocean views alongside the World War II defenses of Fort Miles. Rehoboth Beach and Bethany Beach invite long strolls past boardwalk shops and restaurants. New Castle brings history into focus at the 1732 New Castle Court House Museum, while Odessa preserves colonial treasures such as the Corbit-Sharp House. Farther inland, Hockessin leads to the gardens of Mt. Cuba Center, and Georgetown sits minutes from Redden State Forest. Each town offers a fresh route into Delaware’s beaches, gardens, museums, and centuries of history.
Hockessin
Hockessin stands near the Delaware-Pennsylvania border and boasts a fascinating past that dates back to before its unofficial founding in 1688. Before this time, the land was largely the territory of the Lenape tribe, and while there is some dispute over the origin of the town's name, some believe it comes from the Native American word "hokes." However, most believe it derives from the names of the early properties by the name of "Ocasson," which were settled by William Cox around the year 1726.
The town was and is home to the religious group, which is commonly known as the Quakers or the Religious Society of Friends. The town is still home to the Hockessin Friends Meetinghouse, built back in 1738, which stands on 1501 Old Wilmington Road. It is worth visiting, especially for those who wish to get a glimpse of the community's past. There is also the Hockessin Historical Society, which keeps the town's past alive for locals and tourists to explore and understand. The society preserves Tweed's Tavern, built circa 1790, and the former Lamborn Library, a schoolhouse built in 1870 that later served as a library and community center.
Hockessin sits near some of Delaware's finest nature sites, including the Mt. Cuba Center, the Mason-Dixon Trail, and the Ashland Hawk Watch. The Mt. Cuba Center hosts charming gardens of native plants in an environment full of pretty scenery. Visitors can utilize the online Native Plant Finder to enhance their experience.
Georgetown
Even though Georgetown did not receive official recognition until 1869, the community traces its roots back to after William Penn and Lord Baltimore resolved their land dispute. Although the original county seat of Delaware was down south in Lewes County, the inconvenience of traveling all the way down south encouraged the state to go ahead with plans to move it closer to other official business. In the midst of this border dispute and recognition, Georgetown continued to grow in notoriety as the County Seat of Sussex.
The Georgetown Historical Society operates the Marvel Carriage Museum at 510 South Bedford Street and offers seasonal tours of the Old Sussex County Court House. The Historical Society now has in its possession an 1832 one-room schoolhouse, a 1890 Methodist Church, the Delmarva Telephone Museum, the Sanger Western Auto Museum, and the Boyer Model Train Museum. The town's first train station, known as the Georgetown Train Station, was an important part of the community's early economy. The building dates back to the late 1860s and stands proudly to this day near the Old Firehouse. Visitors can explore the structures during seasonal open houses and Historic Georgetown Association events such as its annual HGA Car Show.
Just a few minutes north of town lies Redden State Forest, Delaware's largest state forest with over 14,000 acres to explore. Redden State Forest has more than 44 miles of trails used for hiking, horseback riding, bicycling, and birdwatching. Travelers hoping to learn a little about the forest can drop by the education center at the historic carriage house on the Headquarters Tract.
Odessa
Odessa is one of the most popular towns in Delaware for history lovers, thanks to the lovely streets still lined with several well-preserved historic buildings. These include sites like Cantwell's Tavern and several residential homes from the 1700s. The lovely colonial town dates back to the arrival of the Dutch in the 1660s, when the area was called by its Native name, Apequinemy. Odessa's dedicated Historic Odessa Foundation, the town's historical society, maintains much of the early structures and grounds.
Visitors can explore the five notable original structures of the region's past, which include the Corbit-Sharp House and the Wilson-Warner House. The Corbit-Sharp House dates back to 1774, meaning it pre-dates the nation's founding, and is one of the foundation's main attractions. Folks can peruse the pretty collection of antique items still available to see on location, which includes historic furniture and beautiful metalwork. The Wilson-Warner House is another well-maintained structure that was built in 1769 and stands right next door to the Corbit-Sharp House. However, the grounds are also filled with beautiful gardens and are ideal for a simple stroll or for hosting a special event.
Moving off the grounds of the Historic Odessa Foundation, spots like Cantwell's Tavern and the Miller-Dunham House offer a step into the town's classy past in a warm and welcoming atmosphere. Cantwell's Tavern dates back to its construction in 1822 and to this day continues to provide nourishing food and a vibrant atmosphere. Built by the Dunhams in 1976 and converted into a bed-and-breakfast in 2017, the Miller-Dunham House now welcomes guests at 207 High Street.
Lewes
Lewes is a pretty little community sitting on an outcropping of land that juts out ever so slightly between the Delaware Bay and the Atlantic Ocean. Its position made it an appealing spot for early Dutch settlers to establish a whaling station after Henry Hudson discovered the region in 1609. However, in 1682, the land of Delaware was given to William Penn, and it became known as Lewes rather than its Dutch name, Swanendael (Valley of the Swans).
Perhaps the town's most famous attraction is Cape Henlopen State Park, which sits just east of the town's border. This park comprises over 5,000 acres of stunning Delaware landscape, including views of the ocean, nature trails, and historical landmarks. Fort Miles, a rich part of southern Delaware's past, was a key point of national defense during World War II. Visitors can explore the Fort Miles Museum to see Battery 519, a 15,000 square-foot underground bunker. The museum houses certain unique artifacts, like the U.S.S. Arizona Relic and the Civil Air Patrol.
Cape Henlopen State Park currently identifies the Biden Environmental Center as its environmental-education facility, and visitors should confirm available programs before arriving. Historic Lewes's 2026 calendar includes the Under Enemy Guns living-history weekend, which commemorates the War of 1812 blockade. Finally, the Lewes Oyster House is a wonderful spot to drop by and get some of the best seafood in town, while indulging in a warm atmosphere.
New Castle
New Castle was home to many people groups over the centuries and has been called by many names over this time. The Lenape Native tribe lived and thrived in much of Delaware long before the arrival of Europeans. Modern-day New Castle took shape after the arrival of Dutch explorers. New Castle was known as Fort Casimir to the Dutch, after they sent Peter Stuyvesant in 1651 to establish the Dutch as having control of local river traffic.
In 1682, the land belonged to William Penn until locals became dissatisfied with his leadership, and he granted them a separate legislature in 1704. At this point in its history, New Castle gained notoriety as the colonial capital of Delaware and remained the county seat until the 1880s. The New Castle Court House Museum is the perfect place to begin exploring the community, since it is part of the First State National Historical Park. First State National Historical Park includes the Brandywine Valley unit and Historic New Castle, where the New Castle Court House Museum is a central historic site.
Built in 1732, the brick structure is a monument to Delaware's fight for independence and is worth exploring. However, the courthouse is just the beginning, and travelers planning their visit can utilize New Castle's virtual walking tours online so they do not miss a thing. Some of the prettiest places to consider visiting include the Dutch House and the Amstel House. With so much to see and experience, tourists to town should book a few nights at the Terry House and refuel at the nearby Jessop's Tavern and Colonial Restaurant.
Bethany Beach
Bethany Beach is one of Delaware's prettiest small towns, situated at the southern end of Delaware along the coast of the Atlantic Ocean. With pristine waters stretching as far as the eye can see to the east, and long stretches of boardwalks with shops and dining to explore, it has a little something for everyone.
The site of modern-day Bethany Beach goes back to the turn of the 20th century, when members of the Christian Church selected it as their own. Although the site was originally intended as an oceanfront gathering spot for Christians all over the nation, it would soon become a full-blown town with the arrival of several businessmen from Pittsburgh in 1902. Today, visitors can learn more about the community's history with the town's Heritage Trail, a self-guided walking tour. While many of the original buildings are no longer standing, there are historic markers along the way that lay out the town as it once was, all while showcasing its beauty today.
The Bethany Boardwalk is a favorite location for shopping, strolling, and taking in the views of the water. The boardwalk is home to the Bethany Beach Boardwalk Arts Festival and the local sweet treat shop, Candy Kitchen. There is also the Bethany Beach Nature Center, one of the best places to better understand local wildlife and trek through marshlands and wooded areas. Lastly, Bethany Beach Runners is a wonderful service for those seeking a restful day out on the sand without the stress of lugging all their beach supplies around all day, thanks to their rental and concierge services.
Milford
Milford is one of Delaware's most artistic towns with an abundance of shops lining its historic streets. Although not established until 1807, its history goes back to 1680 when Henry Bowan settled in what is commonly called the Saw Mill Range. Approximately a hundred years later, Joseph Oliver made his mark in local history by building a dam across the Mispillion River to help create energy for the grist and sawmill.
Throughout the late 1700s, all the way up into the turn of the century, Milford gained a reputation as a prominent shipbuilding town. In its heyday, Milford's downtown area housed six shipyards, with the Albert F. Paul being one of its crowning ships. Sadly, this ship was sunk by a U-Boat in 1942 during World War II; however, its legacy is well preserved in town. The Milford Museum's collections include Milford Shipyards, the Ladybug Room, and A Look at Lou's Bootery, but the museum is temporarily closed while it prepares exhibits at its new 400A NE Front Street location.
Milford's self-guided walking tour takes explorers on a leisurely exploration of several early homes, like the Parson Thorne Mansion, and some early shops and stores, like the site of "The Busy Bee", also known as the Derrickson's Men's Store. Aside from the stunning architecture and vibrant history in town, the Milford Millponds Nature Preserve is located just a few minutes from the community's borders and provides plenty of outdoor excitement for guests of all ages.
Rehoboth Beach
Delaware is known for its beautiful beaches, but Rehoboth Beach certainly takes the spotlight among the state's options. Rehoboth boasts a mile-long boardwalk that overlooks its white sandy beaches, which are known for their beauty and pristine cleanliness. Rehoboth began as a church camp meeting established in 1873 after Rev. Robert W. Todd of St. Paul's Methodist Episcopal Church and others of his community purchased the land from local farmers.
These early origins are still reflected in the community's infrastructure and culture. The modern-day boardwalk traces its roots back to these early days, as well as the Henlopen Hotel and community train station. The current hotel bears the same name as the original structure; however, it was rebuilt in 1974 to accommodate significantly more guests. Although the historic train station no longer runs through its borders, visitors can drop by the Chamber of Commerce Visitors Center and Operating Train to learn more. One of the highlights of this spot is the model train moving along the walls amidst the informative displays.
During the summer months, Rehoboth hosts free concerts every weekend, and it is a great way to mingle with people in town. Biking enthusiasts will love riding along the shore, and more avid cyclists can take the much longer Rehoboth-Lewes Loop on the 15-mile tour of the region. Finally, there is no shortage of shopping and dining experiences to be had in town, either, with some notable spots being Sunny Bay Cafe and the Blue Hen.
Smyrna
Smyrna dates back to the early 1700s, when it was known as Salisbury. However, many called it Duck Creek thanks to its position along the creek by the same name. It evolved from a small community that thrived primarily on shipping agricultural goods via Duck Creek to become a major shipbuilding hub in Delaware. There is some disagreement over how the town's name changed to Smyrna, but most local historians agree it got its name from a Biblical seaport city.
The Henry Levin Center at 27 North Main Street houses a pharmacy museum and conference hall. The site celebrates Smyrna's unique history and serves as a monument to early pharmaceutical research in the United States. From there, guests can travel right down the road to the Allen McLane House. This pretty, historic home stands today on West Mount Vernon Street and has its roots in the American Revolution, with Allen McLane serving in the war for independence. He was a recognized patriot by George Washington, who granted him a promotion to captain.
Lovers of the arts should spend an evening at the Smyrna Opera House, which dates back to 1870. The opera house originally stood to commemorate a sense of togetherness after the American Civil War, and today hosts tribute bands, like a tribute to Earth, Wind, and Fire, as well as art exhibits. Smyrna has several places to eat and drink while walking its historic streets, such as Elizabeth Esther Cafe, Painted Stave Distilling, and S&T Southern Smokehouse BBQ. Each offers guests something unique, including S&T Southern Smokehouse BBQ's slow-smoked pork rib dinner, in a friendly, small-town environment.
Delaware is best known for its pretty beach towns and expansive state and national forests. Highlights include prime locations for sunrise and sunset shots, including Bethany and Rehoboth Beach. However, a truly beautiful and breathtaking location to spot the sunrise and sunset is Cape Henlopen State Park overlooking the sea. Although Delaware's natural wonders take the spotlight, it is the state's history, culture, and close-knit communities that are its warm and welcoming heart.
