
7 Most Charming Town Squares In Delaware
A town square is defined as an open space, often in the city center, with a green area like a park used as a gathering space for the community. They are traditionally surrounded by buildings that are important to functional activities such as town halls, schools, or churches. These types of town squares do not exist in this country in the sense that we imagine them in Europe, but in modern years, town centers have evolved to become more recreational than ever before. In the US today, these socialization centers are often surrounded by local shops, restaurants, and other attractions. Delaware, also known as the "First State," is one of the oldest places in the country, and therefore has plenty of modernized versions of town squares that call it home.
New Castle

New Castle, a town of around five thousand residents, just south of the large city of Wilmington, is situated on the Delaware River. The town has a long and rich early American history, having served as the first capital of Delaware in 1704 until the capital was changed to Dover in 1777, during the Revolutionary War. It is a quiet place, home to lovely Colonial architecture, cobblestone streets, and a waterfront downtown area centered mainly around scenic Battery Park, which serves as its modern-day version of a town square.

Battery Park has lots to offer residents and visitors, including a huge green space, a paved walking trail with three miles of river views, and a children's playground. The park is home to regular town events such as the Wednesday night summer concert series, the Annual Block Party, and Art on the Green. Downtown New Castle has great walkability, too. Around Battery Park, you can easily access multiple local businesses, including Jolt Vintage, a clothing store with affordable prices, Nora Lees, a highly-rated Cajun restaurant, and The Mercury Cafe and Teahouse, a cocktail bar with a unique menu.
Rehoboth Beach

On the Atlantic coast, the tiny town of Rehoboth Beach, which is home to less than two thousand residents full-time, is a booming tourist destination during summer months, with the population swelling sometimes up to twenty thousand people between May and September. Despite this, the town is very quiet most of the year, and it is known for its New England style seaside charm and friendliness, especially toward families with children.
The acting town square of Rehoboth Beach is the gazebo on Rehoboth Avenue right downtown, in the center of the Rehoboth Beach Boardwalk. The gazebo is the location of several fun events, such as the Rehoboth Beach Bandstand Summer Concert Series and the yearly Sea Witch Festival, which is held every October. Lining both Rehoboth Avenue and the boardwalk, you will find endless attractions to choose from, but a few favorites for shopping (which this author can personally vouch for) are Browseabout Books, a locally owned bookstore and variety gift shop, and Penny Lane Mall, an adorable outdoor mall strip with various small independent boutiques.

Located within Penny Lane, you will find the morning time gem Cafe Papillon, a French crepe and coffee shop that also makes delicious fresh pastries daily. For a different kind of sweet treat, The Ice Cream Store is a local legend, with literally a hundred flavors, some of which have very strange names like Booger and Crack. A trip to Rehoboth Beach is simply not complete without going there.
Georgetown

In the southern part of the state, the city of Georgetown is centrally located within driving distance to the state capital of Dover, the US capital of Washington DC, and the capital of Maryland, Baltimore. This makes it a great place to live and visit, being near huge cities while maintaining its calm, suburban feel with only seven thousand residents. Georgetown does have its own unique charm and character, especially known for its significant population of Caribbean immigrants, which helps contribute to its vibrant culinary scene.
The Circle, a traffic roundabout which may look simple at first glance, is actually a long-time focal point of the community, with a pretty curated green space in its center containing a water fountain. Despite being circular in shape, it serves as the town square of the city. Biannually, Georgetown's Return Day Festival is held in The Circle, which is a unique block party celebrating election results. Around The Circle are many small businesses as well, like Maudy's Hispanic Cuisine, a locally recommended Mexican restaurant, Restaurante Mi Laurita, a Guatemalan restaurant, and Georgetown Antiques Market.
Newark

A bigger city with a population of about thirty thousand, in the northern part of the state, is Newark. This is a college town, home to the University of Delaware, and it definitely captures a vibrant, youthful energy. Newark is a hotspot for the arts, offers a diverse food scene, and has well-developed parks and trails, especially around the Newark Reservoir. All of this makes it an attractive city for tourists, and it is well-known among permanent residents as a great place to live, work, and go to school.
Many of the city's attractions are clustered around Main Street, which serves as the city's town square, with a thriving downtown strip and a green space at Frazer Field, which hosts sporting events. Some local favorite things to do in this square include catching a film at Main Street Movies 5, a contemporary theater with top-notch reclining seats and a bar inside, or shopping at the Co-op Farmers Market for locally grown and made products. Or, if you need some immediate sustenance, grab a coffee or baked good at Brew HaHa! or enjoy a bowl of traditional Japanese ramen at Ramen Kumamoto.
Lewes

Nestled in the space where the Delaware Bay meets the Atlantic Ocean, specifically at Cape Henlopen State Park, is the quaint seaside city of Lewes. Just under four thousand people live here full-time, and although summer tourist population increases do occur, the majority of beach-goers head to public ocean beaches like Rehoboth, Dewey, and Bethany Beaches, leaving Lewes to keep its hidden gem status.

The downtown historic district acts as the town square for this small coastal spot, with most of the action gathered around Second Street. Being an old ferry town, Lewes has many buildings which were originally constructed in the 17th and 18th centuries, and a lot of them now host shops and cafes. A few noteworthy small businesses in the neighborhood are Lewes Bake Shoppe, Notting Hill Coffee Roastery, Touch of Italy, and Lewes Oyster House. All of these are locally owned and right within the walkable blocks that make up the modern town square.
Middletown

A slightly bigger town, located just north of Dover, Middletown is a continuously up-and-coming suburban area with charming historic elements as well. Being close to the state capital, it is full of working professionals, young families, and even retirees who are looking for big city convenience without the extra noise. Middletown also has a lovely historic downtown area, like most of the towns on this list, as it was once a popular "tavern stop" for over two centuries before its incorporation in the late 1800s, basically a stopping point for those on their way to already established towns. Many of the old buildings from the late 1800s and early 1900s remain, especially around Middletown's version of the town square.

This aforementioned downtown area is mostly focused around Main Street, specifically near The Everett, an iconic theater which is known for featuring in the cult classic film Dead Poets' Society. Today, the theater still shows both movies and live shows in a historic venue, and it remains a source of entertainment for the community. A few more places worth stopping in around The Everett are the locally-owned Volunteer Brewing Company, Sully's Irish Pub, which is also in an ancient building, or Pithari, one of several Mediterranean restaurants on the same block.
Milford

Located near the Mispillion River, Milford, a town home to around thirteen thousand people, is often considered a gateway to Delaware's beaches, located near many popular stops such as Slaughter Beach and Big Stone Beach. It is generally regarded as a scenic town, surrounded by not just beaches, but also state parks, and being home to a beautiful riverfront trail called Mispillion Riverwalk. It has a wonderful downtown area, concentrated near the Riverwalk mostly around Front Street, which acts as the city's town square.
There are several attractions in that area besides the Riverwalk's stunning green space, including the Milford Museum, packed full of not just local history displays, but also art, as well as an interactive discovery museum. Art thrives in Milford in general, and there are many galleries around the park, such as Gallery 37 and Mispillion Art League. The town hosts regular art-related events as well, mostly at the Riverwalk, like the Milford Holiday Stroll and the Big Draw DE, all intended to highlight local creators and give residents a reason to come out and enjoy themselves.
While Delaware does not necessarily have European-style town squares for the most part, it does have everything that makes those types of town squares so special. In all of the towns on this list and more throughout the state, you will find beautiful historic architecture, like in New Castle and Middletown, incredible waterfront views, like in Lewes and Rehoboth Beach, and most importantly, community. You can be sure that when you stop in these thriving downtown areas, you will encounter new experiences, make friends, and most importantly, have fun.