Red brick early 20th century store front on Market street housing the Red Queen Gallery, Onancock Virginia. Image credit John Blottman via Shutterstock

7 of the Most Quaint Small Towns in the Chesapeake Bay

Welcome to the lovely region of the Chesapeake Bay, the largest estuary in the US, a 200-mile area of land covering parts of six states, most notably Maryland and Virginia. The region was first depicted by Europeans during the 16th century by explorer Diego Gutierrez. Since then, towns and cities have been established, playing host to historic museums, unique celebrations that bring the community together, and high-class restaurant experiences. Spread throughout the region are several quaint small towns, ideal for diving into the maritime history and relaxing in the calm vibes of the Bay-side communities.

Irvington, Virginia

Downtown stores in old homes in Irvington, Virginia
Downtown Irvington, Virginia.

Irvington sits along the Rappahannock River in Virginia. First on the list of stops is the Chesapeake Doughnut Company.  Popular on the menu is the Maple Bacon doughnut topped with maple frosting, and candied bacon crumbles. Upon your exit, travel 1.8 miles to nearby Weems for the Historic Christ Church Museum. The building was first commissioned by Colonial Era Governor Robert Carter under the guise of replacing an outdated church. Today, the well-preserved site tells tourists the story of the church.

If you happen to be in Irvington from May to November, stop by the Farmers Market on the first Saturday of each month between the hours of 9:00 am - 1:00 pm. While listening to live musical acts, sample from the multitude of fresh delicacies from dairy to grain, with even a vendor from Miss Mary's Seafood! One of the places you need to visit is Objects Art and More. What started as a gas station in the 1940s, today, the building is a showcase for art connoisseurs in the region. A trip to the Gallery takes you past artwork from over 200 American artists, and visitors can buy homemade gifts with prices starting at $20.

The Steamboat Era Museum presents bygone-era artifacts, from steamboat models to artwork and photographs. Visitors can listen to stories of figures from that time in history, like African-American Steamboat owner Hansford Bayton, who successfully navigated the Jim Crow era. Finally, for outdoor recreational activity, Irvington has no shortage of opportunities for you! First, hit the links on the 18-hole course at the lovely Golden Eagle Golf Club. Or travel up north, get on the water at Rappahannock River, and fish for species like striped bass, or mackerel.

Havre De Grace, Maryland

Concord Point Light in Havre de Grace, Maryland.
Concord Point Light in Havre de Grace, Maryland.

Located along the Susquehanna River is the town of Havre De Grace. The Decoy Museum is the first stop on your journey, for a history of decoy usage and the creation of decoys within the region. Next up, spend a day on the Bulle Rock Golf Course, host of 5 LPGA championship tournaments. Book your tee time on one of the more visually appealing 18-hole experiences, and stand in the same spots as the pros. Or take a walk along the local trails that connect to the course.

First operational in 1827, the Friends-Concord Point Lighthouse is one of the oldest lighthouses in the state of Maryland. Built with an adjoining Keeper House, the lighthouse is a historical landmark, preserving the history of its years of usage. Visitors can book an in-person tour to navigate the lighthouse property and the keeper's house.

A venture to Mount Felix Vineyard lets you take in a day, embracing its lovely outdoor environment. One of the featured creations of the Vineyard is a lovely Mount Felix Bulle Rock. Before you leave, make sure to stop by the First Call Paranormal & Oddities Museum. The Museum combines unique artifacts from history, such as the infamous figure Hattie Stone, known for killing five members of her family.

Poquoson, Virginia

Workboats parked at the Poquoson Marina.
Workboats at the Poquoson Marina. Image credit Chrisfortier at English Wikipedia, CC BY-SA 3.0, via Wikimedia Commons

Poquoson, Virginia, resides in the Hampton Roads region of the southeastern part of the state. Poquoson is the oldest continuous city name in Virginia, first mentioned in history as a land grant, issued in the year 1631. The first thing for you to do is dine at 1631 Burgers Bourbon & Brew restaurant. You can order from menu items like the bourbon bacon jam burger, made with smoked gouda, house-made pickles, and garlic aioli. The Bourbon Wall features plenty of upper-class varieties, such as a lovely Barrell 15yr.

If you are fortunate enough to be in town during the annual Seafood Festival, then you are in the greatest of luck! Sample from the many delicacies the available food vendors provide, from crab cakes to oysters.  Live musical performances also occur throughout the festivities. For those looking to get outdoors, the Oxford Run Canal Trail is a 1.5-mile venture into the Poquoson outdoors. During your journey, you will walk past the local library, along the local canal, and spot species of birds, such as the solitary sandpiper, during the migration season, or the hermit thrush population during winter.

Through your visit to the Poquoson Museum, gain an education of the local history, from architecture to relevant artifacts showcasing the town's past. Thomas Jefferson Rollins Nature Area is an avid location for bird watching, local to Poquoson. Spend your day in this lovely area, as you walk past unique species like the red-headed woodpecker. A short journey from Poquoson takes you to the Mariners Museum. Located in nearby Newport News, get lost amongst the lovely 550-acre landscape. During your experience, stop along the Monitor Overlook, which presents a picturesque view of the Museum's architecture.

St. Michaels, Maryland

Part of St. Michaels Harbor in historic Saint Michaels, Maryland, in spring
St. Michaels Harbor in historic Saint Michaels, Maryland.

The town of St. Michaels rests on Marylands' eastern shore, just a two-hour drive from Washington, DC. St. Michaels was a significant setting during the War of 1812, as its residents deployed a rather unique gambit while facing British bombardment. They took several available lanterns and hoisted them into the trees. This played a role in misdirecting the British attacks, as most of their homes were protected. As a result, "The Town That Fooled the British" became a name synonymous with St. Michaels. 

Operational since 1965, the Chesapeake Bay Maritime Museum is an 18-acre building in St. Michaels. The Museum takes you across several public exhibitions, as you learn the local history of steamboats, as well as other stories, like oystering. The Classic Motor Museum is a local collection of old cars, primarily from the pre and post WWII, eras. During your trip to the Museum's "Exhibit Barn," walk amongst well-preserved antiques like a 1917 Maxwell or a 1931 American La France Firetruck.

The Ghost Walk is an experience you must undertake while in St. Michaels. Be prepared as you walk past the haunted properties, from buildings to a graveyard, on a night to remember. St. Michaels Brewfest is a staple celebration for the local community. The price of admission lets you wander through all three event venues. So come one, come all, and sample the available brews from seasonal to one-off brands, all provided by local breweries.

Patriot Cruises is the best way to get out on the water. Your afternoon will show you the region's historical charm as you spend 65 to 70 minutes relaxing with an available beverage of choice.

Onancock, Virginia

Downtown street in Onancock, Virginia.
Downtown Onancock, Virginia.

In the Accomack County region of Virginia lies the town of Onancock, 15 miles to the southwest of Mappsville. Upon arriving in Onancock, set forth on a venture to the historic Ker Place. It was first designed in 1803 as a home for merchant farmer John Ker. Today, the fully restored mansion is home to the Eastern Shore of Virginia Historical Society.

The North Street Playhouse is where you want to be if you have an interest in the theater, as it is the only regular live theater location on the Eastern Shore of Virginia. Operational since 1986, the playhouse has become a popular location to spend an evening watching the performing arts. The Eastern Shore Watermen's Museum & Research Center dedicates itself to preserving the history that is Virginia's Eastern Shore. Housed in the museum is a large collection of archival material, from 45,000 digitized photos, to boat replicas, and other relevant artifacts to the local history.   

If you are in the area, from May to the end of October, you must take a ride on the Tangier-Onancock Ferry. Spend a lovely day on Tangier Island and sample the delicious chicken salad at Four Brothers Crab Shack. The gallery of internationally recognized artist Danny Doughty is local to Onancock. It is an exhibit full of Doughty's creations, such as "Mommas Grapevine." You can connect with Doughty himself and learn his secrets.

Crisfield, Maryland

Chesapeake Bay sunset near Crisfield, Maryland.
Chesapeake Bay sunset near Crisfield, Maryland.

Along Little Annemessex River in Somerset County Maryland, is the town of Crisfield. Stop by the J. Millard Tawes Museum as you explore local history, preserved by the Crisfield Heritage Foundation. Crisfield is often called the "Crab Capital of the world," and the town celebrates through the annual National Hard Crab Derby. Events range from, musical entertainment, to a beauty pageant, and the annual Mike Sterling race.

Your journey to Janes Island State Park will allow for a lovely day of relaxing. The campgrounds offer several campsites, a number with electrical hook-ups for visitors. The other section of the park is an undeveloped area of land, with space to enjoy pristine beaches or spend a day, fishing, crabbing, or simply sitting in the sun. The Cedar Island State Wildlife Management Area is a short drive from Crisfield. While other species of wildlife reside in this region of land, the most popular attraction is the population of black ducks.

The Somers Cove Marina is a well-developed harbor in Crisfield. Visitors receive a charming rest as they escape the confines of their docked vessels. They can spend their day enjoying the relaxing swimming pool and adjoining gift shop. The Marina is also close to nearby shopping and restaurants. The Red Shell Shanty is a popular restaurant in the Somers Cove Marina. From delicious sandwiches to thirst-quenching beverages it is the perfect place to dine.

Kilmarnock, Virginia

Street corner in downtown Kilmarnock, Virginia
Downtown Kilmarnock, Virginia.

The town of Kilmarnock is in the Northern Neck Peninsula of Virginia. First settled in the 1600s, it was initially nicknamed "The Crossroads," likely for an intersection of multiple Indian pathways. The Kilmarnock Antique Gallery is a vintage shop, home to a lovely collection of vintage oyster plates. It is a large establishment, with over 100 antique dealers and an area of 22,000 square feet. 

The Hughlett Point Natural Area Preserve is a diverse region of land, known for its varying species, from bald eagles to northern harriers. Visitors are able to access the local habitats and traverse a series of designated trails. Kilmarnock is a town that can embrace the Christmas spirit! The annual Lighted Christmas Parade is a 40-year staple to the community, as the people are united together under a lovely evening sky.

The Kilmarnock Town Centre Park has amenities for the whole family. While visiting, you can spend your day playing in the local splash park or relaxing in the picnic area. The Half Shell Stage is the primary attraction as from May to October; it hosts live music from a variety of genres. You are beholden to stop at the local Northern Neck Popcorn Bag establishment. Sample from a wide variety of their distinct creations, like the Rainbow Popcorn, a colorful design filled with several unique flavors.

There are many ways to connect with the uniqueness of the Chesapeake Bay. Learn the history of decoys, at the Decoy Museum in Havre De Grace, Maryland, or explore the Ker Place, preserving the local history of Onancock, Virginia. The lovely Bay region is an ideal way to take in the breathtaking atmosphere, sample the local cuisine, or step across several historical landmarks. So stop what you are doing now and book your trip; you will not regret your decision!

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