Aerial view of St. Michaels, Maryland.

These Towns In Chesapeake Bay Come Alive In Spring

As the largest estuary in America, the Chesapeake Bay is a 320-mile-long coastal body of brackish water that drains into New York, Pennsylvania, Delaware, Maryland, Virginia, West Virginia, and Washington, D.C. Directly bordering the bay are Maryland and Virginia, which derive natural and cultural nourishment that fuel springtime festivities in small shoreline communities. From a pirate invasion to a countryside art festival, take a peek at a spirited spring in the Chesapeake.

Yorktown, Virginia

Aerial view of Yorktown, Virginia.
Aerial view of the beautiful beach at Yorktown, Virginia.

Located where the Chesapeake Bay meets the York River, Yorktown was an essential port in colonial America and helped secure the country's independence during the Revolutionary War. Thus, modern Yorktown honors its maritime heritage with static attractions like the American Revolution Museum and annual waterfront events such as those that occur in spring. During late April, pirates invade Yorktown for Pirates Invade Yorktown, a weekend's worth of blacksmithing, cannon firing, shanty singing, and treasure hunting. May brings both the Blues, Brews & BBQ Festival and the Art at the River Juried Art Show, while Yorktown Market Days revitalize Riverwalk Landing with produce, seafood, soap, candles, and much more from April all the way to October.

Cambridge, Maryland

The harbor in Cambridge, Maryland
The harbor in Cambridge, Maryland.

Another historic Chesapeake community, but this one on Maryland's Eastern Shore, Cambridge, has several heritage sites that open for tours in spring. These include the Choptank River Lighthouse, a replica of an early-20th-century illuminated icon that can be toured between May 1 and October 31 (private tours can be arranged by appointment in off-months), as well as the Richardson Maritime Museum, which is expected to reopen in early 2024. While awaiting those attractions, you can check out April events like the Cambridge Main Street Spring Fling, Cambridge Farmers' Market, Cambridge Craft Market, and Food Drive, and Guided Birding Tour at Blackwater National Wildlife Refuge. In addition to migratory, song, and shore birds, one can see frogs, toads, flowers, and many other kinds of colorful wildlife while trekking through nearby Blackwater in spring. Also, if you visit in mid-March, you can admire Blackwater's bald eagles at the annual Eagle Festival.

Solomons, Maryland

Boardwalk in Solomon's Island, Maryland,
Boardwalk in Solomon's Island, Maryland, on the Patuxent River.

A Western Shore community, Solomons is the spring king of that domain. Events have included or are expected to include the Fairy & Gnome Home Festival at the Annmarie Sculpture Garden & Arts Center, Spring & Craft Vendor Show at the Solomons Volunteer Rescue Squad and Fire Department, and Solomons Sunset Sail at Fisherman's Wharf. But many of Solomons' biggest spring flings come courtesy of the Calvert Marine Museum, a preserve of paleobiology, modern estuarine life, and human maritime history. During the milder months, it hosts everything from OtterMania! to the Fossil Egg Hunt to the Spring Jewelry Trunk Show to the Solomons Maritime Festival, whose highlight is an antique boat and marine show.

Urbanna, Virginia

Urbanna Creek in Urbanna, Virginia
Urbanna Creek in Urbanna, Virginia.

Although Urbanna is known as a fall destination, since it draws roughly 75,000 visitors for November's Urbanna Oyster Festival, it does not clam up in spring. In fact, this 500ish-person town has several spring-enlivened attractions, including the Urbanna James Mills Scottish Factor Store Museum & Visitor Center, which is a restored 18th-century building that opens for extended tours in May. Urbanna is also the site of multiple springtime festivals. The first, Arts in the Middle, ushers in June with two days of art and fun at the Hewick Plantation. The second, Urbanna's 2nd Saturdays, brings music, crafts, and food to Taber Park on the second Saturday of May, June, July, August, and September.

St. Michaels, Maryland

The harbor at St. Michaels, Maryland
The harbor at St. Michaels, Maryland.

St. Michaels is arguably the Chesapeake spring festival mecca. This Eastern Shore town has just over 1,000 residents but attracts thousands of spring breakers for the Taste of St. Michaels Tasting Crawl, St. Michaels Running Festival, St. Michaels Brewfest, Classic Motor Museum Memorial Day Parade, Eastern Shore Sea Glass & Coastal Arts Festival, and Antique & Classic Boat Festival & Coastal Arts Fair. The last two fests are held at the Chesapeake Bay Maritime Museum, which is an 18-acre waterfront collection of buildings, ships, and artifacts that can - and should - be visited year-round.

Onancock, Virginia

Market Street in Onancock, Virginia
Market Street in Onancock, Virginia. Editorial credit: John Blottman /

Onancock is another tiny Chesapeake town with a historic venue that overflows with spring events. The Historic Onancock School is a 103-year-old building on a 13-acre estate that is set to host the Field Day Fiesta on May 4, Blooms and Brushes Garden and Studio Tour on June 8, and Wine Wednesday on the first Wednesday of each month. Non-school-held spring festivities include Music on the Lawn Sunshine & Margaritas, which is scheduled for May 24 at Ker Place, and the Second Friday Art Stroll, which runs (strolls?) at the Onancock Business & Civic Association on the second Friday of each month.

Stevensville, Maryland

Matapeake Fishing Pier on the Chesapeake Bay in Stevensville, Maryland
Matapeake Fishing Pier on the Chesapeake Bay in Stevensville, Maryland.

Situated on Kent Island, Stevensville hosts Kent Island Day, a celebration of the island's 1631 founding that is held on the third Saturday of May. While coming alive with historic exhibits on Main Street, this community also comes alive with wildlife at Terrapin Nature Park, which spans 276 acres and contains a 3.25-mile oyster chaff walking trail, wildflower meadows, and approximately 250 species of birds. From Terrapin, a short drive inland takes spring peepers to the vibrant Adkins Arboretum. Beyond 600 species of native plants, the arboretum offers an array of vernal activities like birding, foraging, nature journaling, and botanical drawing.

Chestertown, Maryland

The Business District in Chestertown, Maryland
The Business District in Chestertown, Maryland. Editorial credit: George Sheldon /

Chestertown connects to the Chesapeake Bay via the Chester River, which is where tea was allegedly dumped in 1774 and resulted in one of the biggest spring celebrations in the region. The Chestertown Tea Party Festival is held each Memorial Day Weekend on the anniversary of America's lesser-known and little-documented Tea Party, where Chestertownians are said to have tossed tea cargo into the river to protest British rule. A tea toss reenactment headlines the fest, which also features music, crafts, races, street performances, children's activities, a parade, block party, and even a semi-separate Beer Fest.

As stylish as it is historical, Chestertown's other springtime spectacles revolve around art. The Chestertown A&E Spring Art Walk brings dozens of artists together for one sketch-filled mid-April day, while Paint The Town paradoxically takes artists into the country for three late April days of scenic painting before displaying those pieces in the RiverArts Gallery.

The Chesapeake Bay is a massive American estuary that fuels spring activities. Being direct recipients of the bay's bounty, shoreline towns in Maryland and Virginia come alive with plants, animals, and humans from March to June. Yorktown, Cambridge, Solomons, Urbanna, St. Michaels, Onancock, Stevensville, and Chestertown are eight of the best places for interspecies partying during a Chesapeake spring break.

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