11 Most Charming Town Squares In Chesapeake Bay
The Chesapeake Bay is the largest estuary in the US, and its coastal towns and villages make it a distinctive place to visit. These are among the most scenic towns on the Chesapeake Bay, each displaying historical sites, fun venues, and coastal charm. There are many things to do and see in these areas, and each one reflects the best aspects of this beautiful region.
The historic diversity of Chesapeake Bay is another fascinating aspect to consider before visiting. Hamlets like Annapolis are steeped in military history, while Havre de Grace is known for its architectural styles and lighthouse. Whether looking for a weekend of shopping or a historic excursion, these are the 11 most charming town squares on the Chesapeake Bay.
Havre de Grace, Maryland
Downtown Havre de Grace is filled with historic commercial buildings, charming boutiques, and unique finds around every corner. The walkable area offers waterfront views and many museums and galleries that honor the storied legacy of the area. The Havre de Grace Colored School Museum & Cultural Center celebrates the legacy of those who advocated for equitable access to education for African American students in Harford County in a building over 100 years old.
Other attractions include Arts by the Bay: An Artists’ Cooperative Gallery, featuring regional work and annual events like the Martinis with Money fund-raising event. After a day of discovering downtown, it is time to grab a bite and unwind. Unsurprisingly, there are many dining options available, including the fun Abbey Burger. The brick structure is typical of the area's architecture, lending award-winning burgers and rotating exotic meats a historical flair that matches the menu perfectly.
Easton, Maryland
Shops and galleries line downtown Easton's streets, and the lively community hosts many events celebrating the area and the people that make it so unique, like First Friday Art Walk, a prime opportunity to get to know the locals and shop with local vendors. There is a lot to celebrate here, from Victorian architecture to stunning views of the Eastern Shore, and this is one of the best towns along the shore to unwind in.
Guided walking tours are available to see Federalist buildings in the Historic District, as well as the Ebenezer Methodist Episcopal Church. Each one provides a fascinating study of Easton's past and tells the story of the town's evolution into what it is today. Although there is much to see and do, one would be remiss not to go to the Chesapeake Bay Maritime Museum to learn about life on the bay and how it has supported generations of mariners and their families.
Oxford, Maryland
Historic and charming Oxford is a colonial port known for its Victorian architecture, low-key atmosphere, and virtually endless attractions. It is a relaxing place, though there is much to see and do. For an ultimate stay, consider a room at the 1710 Robert Morris Inn, the oldest full-service inn in the US, in the heart of town. While in a historic frame of mind, be sure to explore the Oxford picket fences. The pickets are hand-painted with different floral scenes, adding an artistic flair to the historic district.
Maps to the fences can be picked up at the Oxford Museum, which the residents founded to preserve over 300 years of exhibits and history from the area. Afternoons and the Scottish Highlands Creamery are an ideal pair. The ice cream shop, voted among the top 5 in the US on TripAdvisor, offers the best daytime desserts that complement the seaside town perfectly.
Chesapeake City, Maryland
Downtown Chesapeake City is a historic seaside village known for its 19th-century architecture and for its connection between the Chesapeake Bay and the Delaware River. It is also the only Maryland town on a working commercial canal. This history and others are detailed at the Chesapeake City Museum through artifacts and exhibits, providing an insider's look into this fascinating heritage and culture.
The Donald Pell Gardens is another stunning feature downtown. It is a lush botanical garden with tall grasses and multi-colored flowers, providing a peaceful respite in the middle of the day. Before getting the day started, stop at Cafe on the Bay, a coffee and breakfast spot with a cozy atmosphere and incredible views. This atmosphere sets the tone for a day spent in this historical coastal city.
Solomons, Maryland
Solomons, also known as Solomons Island, is a charming coastal village with a cozy downtown, featuring historical and culinary attractions that set it apart from other bay towns. A popular downtown spot is the Solomons Island Boardwalk, featuring views of the Patuxent River and access to various restaurants and coastal shops, all in the heart of downtown. The area is also a hub for arts and entertainment.
Annmarie Sculpture and Arts Garden combines the best regional art, sculptures, and nature for a unique venue that the whole family will love. Calvert Marine Museum is another top destination, featuring hands-on exhibits about the local marine ecosystem that are both fun and educational. Solomons is that rare place where visitors can feel the uniqueness and the efforts the community has put into making the entertainment and cultural centers so inviting, and it should top every traveler's list for places to go in Maryland.
Annapolis, Maryland
Annapolis is rightfully famous for being home to the United States Military Academy, but it also has a fantastic shopping district that brings visitors in from all over. The walkable district centers on Main Street and is bordered by buildings over 300 years old. Main Street leads to the charming City Docks, an ideal location for sipping on a coffee and watching the harbor traffic before heading out for some retail therapy.
Annapolis Town Center is a central hub for shopping and dining. It includes box stores and boutiques, such as Kendall-Jackson. The amalgamation of history, modern retailers, and legislation is a key feature of downtown Annapolis. Just past the shopping center is State Circle, where visitors can catch a glimpse of the Maryland State House before they continue their trek in one of the most entertaining districts on the bay.
Saint Michaels, Maryland
Downtown Saint Michaels is a historic district, notable for its waterfront views, boutiques, and maritime centers, such as the Chesapeake Bay Maritime Museum. Talbot Street is the main drag, the center of activity for locals and visitors alike. The red brick sidewalks winding past Victorian homes make the village look and feel like a 19th-century seaport.
Downtown is also a haven for dining, featuring everything from casual to romantic fare. An excellent choice for the latter is Bistro Saint Michaels, offering a chef-forward menu with the best ingredients and traditional culinary techniques for a classy meal while out on the town. To complete the ambiance, book a room at Two Swan Inn & Cottages, a historic inn built in 1790 with gorgeous waterfront views.
Chestertown, Maryland
Chestertown's downtown is a historic district with 19th-century homes, modern art galleries, and picturesque views of the harbor. It is also part of the Main Street Historic Chestertown revitalization project, underscoring its importance to the region and the community's efforts to promote its sustainability. A self-guided historic walking tour is the best way to be introduced to Chestertown and its many sites, including the first college in the nation to be founded after the Declaration of Independence, Washington College.
Other notable sites include a section with mostly Georgian-style buildings, which were popular until 1830, such as the Widehall Building. Every architectural style is visible here, a telltale sign of the era in which the buildings were constructed, and it is a fascinating way to experience a historic place like Chestertown. Point in fact, Stam's Hall is an excellent example of the French-inspired Second Empire style, popular in the late 19th century. Looking at the town this way helps connect the dots from one era to another, and this antiquated seaport is a perfect example.
Cape Charles, Virginia
Historic Cape Charles's Main Street area is filled with classic brick buildings, historic sites, and modern venues on Virginia's Eastern Shore. The friendly atmosphere is warm and inviting, and walking around the area is a great way to experience the best it has to offer. A notable historic structure is the Palace Theatre, which has been open since 1942 and is a landmark of the historic district centered on Mason Street.
Booking a room at the Fig Street Inn is an excellent choice for staying in the heart of the historic district, close to restaurants and retailers. The boutique bed and breakfast offers luxury accommodations in a comfortable setting that lets guests get the most out of any visit to Cape Charles. Aviation enthusiasts will not want to miss At Altitude Gallery on Mason Avenue, featuring aerial photography of the Chesapeake Bay region that provides a literal bird's-eye view.
Irvington, Virginia
Downtown Irvington is compact with a cozy atmosphere and many cultural attractions. One particular venue showcasing a part of the region that many do not know about is the Dog and Oyster Vineyard, a micro vineyard whose quirky name comes from the dogs who rescue the grapes from deer and other wildlife, and which honors one of Chesapeake Bay's treasured assets. It is a great place to spend an evening in one of the most charming districts on the bay.
Visiting the Steamboat Era Museum is a fun and educational way to discover the vitality of the Chesapeake Bay in these small towns, even today. The gallery is next to the Commons, a central gathering place for residents and visitors. This gathering hub makes the town even more appealing and, combined with its interesting venues, makes it one of the best to visit on the coast.
Onancock, Virginia
Onancock's Main Street area is an artsy and walkable district known for its many galleries, restaurants, and shops. Landmark sites to visit include the 1700 Federalist-style mansion Ker Place, long considered the finest example on Virginia's Eastern Shore. Newer historical sites are just as interesting, including the Roseland Theater.
Movie buffs will appreciate the neon lights and Art Deco design of this retro theater, which offers an entertaining way to spend an evening in town. And of course, Onancock has plenty of dining options downtown. Popular spots include Mallards at the Wharf, featuring waterfront dining in a laid-back atmosphere that captures the town's character.
From the Naval history and shopping malls of Annapolis to bucolic Irvington, these are the 11 most charming town squares in the Chesapeake Bay. While each hamlet boasts its own distinctive characteristics, they all share inviting communities and attractions, making them among the best places to visit in the area. History is virtually everywhere, from commercial structures to historic sites, adding to the region's appeal.
The compact roads are easy to walk on, making them the best option for visiting these neighborhoods. A slower pace allows more time to absorb the area's uniqueness and take in the salty breezes. Many places celebrate this singular atmosphere, especially the restaurants specializing in local seafood and live music. Town squares are the hub of all activity and the best places to immerse oneself in local culture.
