9 Standout Main Streets On The Chesapeake Bay
Chesapeake Bay is the largest inlet along the Atlantic Coastal Plain and is bordered by the two states of Virginia and Maryland. Originally settled in the early 17th century, this region has witnessed numerous historical events, including the War of 1812 and the Civil War. Given its extensive history, these towns have grown and thrived, and each has developed its own vibrant culture. The unique facets of these towns can be seen on their main streets, making them incredible destinations if you are in the Chesapeake Bay area.
St. Michaels, Maryland
St. Michaels is situated on the Miles River, and residents know Talbot Street as the main thoroughfare of the city. Dining and shopping options are plentiful and found just minutes from the river. Restaurants like Limoncello create a unique vibe by evoking an Italian bistro that serves alongside wines and spirits. Down the street, St. Michael's Fine Woodworking crafts high-quality furniture, including tables, benches, and cabinetry.
Just steps off Talbot, you can find the St. Michaels Museum. Artifacts at the museum depict the history of local business and the growth of St. Michael's along the bay from its time as a small trading post. Those who want to take a short jaunt to the river will find great photo opportunities at the Hooper Strait Lighthouse, which was originally built in 1879 and today preserves the history of the Chesapeake Bay and the maritime life on its waters.
Annapolis, Maryland
Few places have as vibrant a downtown core as Annapolis. Main Street runs from Annapolis Harbor in the east to Church Circle, before splitting off into College Avenue and West Street. Main Street proper boasts a stretch of dining and shopping destinations, including Hats in the Belfry, a unique hat store specializing in a variety of styles. Those looking for an early meal may prefer Café Normandie, a café featuring French wines and weekend breakfast.
Just steps away on West Street, visitors can find Rams Head On Stage, a live music venue with acts ranging from Motown performers to orchestral ensembles. On the opposite side of Main Street, along Spa Creek, visitors can find the Museum of Historic Annapolis, which documents the city's history dating back to the days of the Revolutionary War.
Havre de Grace, Maryland
Havre de Grace has been a Maryland Main Street community for two decades, a program that attempts to strengthen the economy of main streets in the state. When people think about what the official main street is, they usually think about the stretch of town that runs along St. John Street and down Market Street. Graw Alley Public Art Park can be found along this stretch. It is an interactive park in Harmer's Town Art Center that features sculptures and murals along landscaped pathways.
Not far away, charming photo opportunities await at the Concord Point Lighthouse. The lighthouse has been standing since 1827 and today is the oldest lighthouse accessible to the public on the Chesapeake Bay. Just down the street in Millard Tydings Memorial Park, visitors can walk the riverfront before arriving at The Promenade Grille. This restaurant is the perfect dining spot for those who want to enjoy views of the bay in a casual, comfortable environment.
Oxford, Maryland
Oxford is a small town that lacks a traditional main street, but it boasts a beautiful waterfront where the majority of its shops are concentrated. Visitors to the area will want to head to South Morris Street, which runs parallel to the Tred Avon River. Here, you will find The Treasure Chest, a unique store specializing in the sale of works by local artisans, as well as nautical-themed home décor.
Right across the street, you will find Oxford Town Park, a popular destination where guests can enjoy walks along the waterfront and some of the most scenic views in town. Just steps away, you will also find The Oxford Museum. The exhibits at the museum constantly change, and while they often focus on the history of Oxford, some exhibits are themed around holidays or other fun activities, such as the popular hobby of assembling model trains.
Chesapeake City, Maryland
Chesapeake City has its origins in the 17th century, when settlers first arrived in the Bay Area. Currently, the only town in Maryland that sits along a working commercial canal, people often come for the views along the creek. Bohemia Avenue is a popular stretch with a string of dining and shopping options. Visitors to the area will want to stay at the Inn at the Canal, where guests can enjoy a stay in a 19th-century home boasting Victorian architecture.
Just outside, you will find The Mercantile at Back Creek, home to an array of interesting jewelry, gifts, pottery, and more. At the far end of the avenue, The Bayard House Restaurant is a unique dining spot along the water where seafood is served in an 18th-century house. Diners can have a drink along the creek while listening to weekly live music.
Cape Charles, Virginia
Cape Charles' main street, known as Mason Avenue, is the go-to destination for shoppers and those looking for a bite to eat. Unique accessories can be purchased at Moonrise Jewelry before a stop at nearby Ambrogia Caffe, where guests can enjoy Italian cuisine, dolci desserts, and wine. Only steps away, you can find the Lemon Tree Gallery and Studio, a curated collection of paintings, sculptures, jewelry, and gifts to take home. At the far end of Mason Avenue, you will come upon Cape Charles Beach. After shopping along the avenue, you can take in perfect views of Cape Charles Harbour and even cast a line from the fishing pier.
Yorktown, Virginia
Yorktown's official Main Street, which cuts through town, is a hub for historic destinations. The Yorktown Victory Monument rises from adjacent Yorktown Park to commemorate the Revolutionary War. As you walk down Main Street, you can find the Dudley Digges House, first erected in 1760, among other historical houses. York Hall serves as the town's museum, as well as a gallery and welcome center, showcasing the region's history and heritage.
Meanwhile, Water Street acts as a sort of second main street. It runs along the waterfront and is the ideal location to find a variety of shopping and dining options. Yorktown Beach is also accessible from Water Street for those who want to hit the water. Fortunately, Water Street and Main Street are only a block apart, making it easy to enjoy not only the history of Yorktown but also its many recreational options along the York River.
Onancock, Virginia
Onancock is a member of the Virginia Main Street program, which aims to promote local businesses and culture. Market Street is the main thoroughfare in town, featuring not only shopping and dining spots but also galleries and historic destinations. Just steps off of Market Street, you can find Ker Place. This elegant 18th-century property serves as a museum, showcasing the region's history through artifacts and archives, as well as period furnishings in a stunning architectural landmark.
Nearby are several galleries, including the Crockett Gallery, which features themed collections that showcase natural landscapes, including those of the Chesapeake Bay. At the end of the street, Mallards at the Wharf serves up seafood with perfect views of Onancock Creek. Before or after a meal, visitors can head next door to Burnham Guides to set out on the water by kayak or SUP, or rent bikes to explore the region's trails.
Kilmarnock, Virginia
Kilmarnock is located just a short distance from the Chesapeake Bay, and despite its small size, it enjoys a vibrant Main Street. The Kilmarnock Inn is just steps off Main Street and makes for the perfect way to enjoy a stay in town. The main cottage was first constructed in 1884, and today, guests can enjoy stays in one of the many cottages on the grounds, as well as dine at Filibuster's Restaurant.
On Main Street proper, there is no shortage of places to eat and shop. Those seeking unique pieces for their home will want to visit Rivah Antiques and Accessories to discover paintings, wooden figures, and more. Further down the road, guests can find the Kilmarnock Museum, situated in one of the town's oldest buildings. Today, visitors can stop by and discover artifacts that depict the area's history, with an emphasis on three devastating fires that swept the region during the early 1900s.
Main Streets Across The Chesapeake Bay
The Chesapeake Bay region is a diverse area filled with small towns that each exude their own unique charm. The main streets of these towns are worthy destinations in their own right. Some boast numerous historical landmarks, such as Ker Place and the Yorktown Victory Monument, while others are filled with shopping and dining destinations. The next time you are in the Chesapeake Bay area, carve out some time to explore these small towns and their main streets.
