Chesapeake Bay's Best Small Towns for a Weekend Escape

Sometimes, you just need to escape the rat race and get out of town. When the urge strikes, head for the Chesapeake Bay — the perfect getaway for an idyllic weekend break. America’s largest estuary, Chesapeake Bay, stretches almost 200 miles from Maryland in the north to Virginia in the south, giving travelers plenty of options when selecting their weekend escape. The area is packed with welcoming small towns, sandy beaches, and scenic shorelines. Breathing in the fresh bay air and strolling the tree-lined main streets of the many inviting Chesapeake Bay communities, you will forget all about the daily grind and return home refreshed and renewed.

Havre de Grace, Maryland

Right at the top of Chesapeake Bay in Havre de Grace, a tranquil town with lots to explore and see. Start with the Havre de Grace Maritime Museum, which covers the town’s extensive history from its early Native American inhabitants through the War of 1812 and up to the present day. On a sunny day, there’s no better place to enjoy the town than from the waterfront boardwalk, which winds along the Susquehanna River as it joins the Bay and meanders past boutique shops and bustling cafes.

For a picture-perfect moment, catch the sunset at the Concord Point Lighthouse, built in 1827 and the second oldest lighthouse in Maryland. Near the lighthouse, you’ll find the Vandiver Inn, a historic home just blocks from the water. This award-winning inn is a popular spot for romantic getaways thanks to its beautiful surroundings, fine dining, and luxury amenities.

Cape Charles, Virginia

Cape Charles may be a small town, but there’s lots to keep you busy for a weekend. Rent a stand-up paddleboard or a kayak and launch from the town beach to enjoy the water. If you’re looking for more adventure, try kiteboarding. The Bay breezes make this the perfect spot to try the sport. Book a cruise around the Bay to see some of the area’s aquatic residents — a school of lively dolphins who often pop up to greet tourists. Wandering around downtown, you’ll see gorgeous historic homes, some of which date back to the 1800s.

Cape Charles is home to the oldest library on Virginia’s Eastern Shore, the Cape Charles Memorial Library, and the historic Palace Theatre, a classic example of Art Deco architecture. In the heart of historic downtown, you’ll find Central Park. This green oasis was redesigned in 2010 to include a pergola, a gazebo, and a cascading fountain. If you’re looking for somewhere cozy and welcoming to stay, consider the Bay Haven Inn, a gorgeous 1906-built property with period furnishings and conveniently located a short walk from downtown.

Irvington, Virginia

Irvington is a top destination for foodies and nature lovers. The town is famous for its Rappahannock River oysters, which you can sample at The Dog and Oyster Micro-Vineyard. This popular raw oyster bar pairs fresh oysters with the perfect local wine for a truly unique dining experience. Nearby is the Hope and Glory Inn, a beautiful B&B consisting of six suites and seven cottages on the grounds of a former 19th-century schoolhouse. For a closer look into Irvington’s rich heritage, visit the Steamboat Era Museum downtown and the Historic Christ Church Museum, a small parish church completed in 1735.

Chestertown, Maryland

Located on the banks of the Chester River, Chestertown is a bustling but historic town that’s a perfect blend of old-world charm and modern buzz. Strolling down the main street, you’ll see examples of the town’s thriving arts scene in its many boutiques and galleries. In the heart of downtown is Fountain Park, named for its quirky centerpiece — an ornate fountain depicting the Greek goddess Hebe and a local landmark since 1899.

Head to the waterfront, and you can’t miss the Sultana, an exact replica of a 1768 schooner. The Sultana runs two-hour sailing tours down the Chester River on intermittent weekends from May to October. If you’re looking for somewhere to stay, the White Swan Inn is a traveler's favorite, as well as a local historic landmark. The elegant colonial-era inn is just steps from downtown and the waterfront.

Tappahannock, Virginia

A pretty town on the Rappahannock River, Tappahannock is one of the area’s most historic communities, first established in 1682. Step back in Tappahannock’s past with a self-guided walking tour around the town’s historic district. This guided trail takes you past landmarks such as the Old Debtors Prison and Derieux-Scots Arms Tavern, which was built in 1680 and is now the oldest privately owned home in town. Explore the river from Rappahannock River Park, the perfect spot for a waterside picnic on a sunny day or catch the wildlife at the Rappahannock River Valley National Wildlife Refuge.

Here, you can see soaring bald eagles, lively white-tailed deer, and dazzling monarch butterflies stopping for a break during their annual migration. If, like the Monarchs, you’re in need of a break, head for Caret Cellars, a family-owned vineyard and winery with regular weekend tastings. When it comes to accommodation, The Essex Inn is a boutique B&B with plenty of Virginia hospitality and old-fashioned comfort. Across the street is the Inn’s newly-opened eaterie, 1710 Tavern, which is housed in a stunning century-old tavern.

Chesapeake Beach, Maryland

We all need a bit of pampering sometimes, so treat yourself and that special someone to a weekend at Chesapeake Beach, a beachfront resort destination that’s all about rest and relaxation. Soak up the sun at Breezy Point Beach, a pretty waterfront recreation area and campground, or rent a cabana at the Chesapeake Beach Water Park.

Get moving and enjoy the serenity of nature with a gentle hike along the Chesapeake Beach Railway Trail, two miles of lush gardens, birding platforms, and ecology exhibits. The trail follows the old railway tracks, and you can learn more about the history of this key transportation route at the charming Railway Museum, housed in an 1898 railway depot. For the ultimate in relaxation, stay at the Rod N’ Reel Resort, a waterfront hotel that offers ocean views, a rooftop pool, and a full-service spa.

St. Michaels, Maryland

Enjoy a weekend of luxury in St. Michaels at the Inn at Perry Cabin by Belmond. Occupying 25 acres of waterfront in the historic maritime town, the Inn includes a therapeutic spa, an 18-hole championship golf course, and extensive grounds from which you can sit and watch the sailboats glide by. It’s the perfect storybook setting for a lakeside retreat, but don’t forget to venture outside the grounds to explore the town.

St. Michaels has a rich maritime history, documented at the 18-acre Chesapeake Maritime Museum. Away from the waterfront, you’ll find funky boutiques, antique shops, art galleries, and craft breweries, including the Eastern Shore Brewing Company, which offers rotating seasonal specialties.

Relax and Recharge in Chesapeake Bay

Whether you’re planning a girls' weekend, a romantic retreat, or simply a much-needed break from work, Chesapeake Bay has something to suit every taste. Cozy colonial inns, peaceful shorefront parks, quaint main streets, and unforgettable historical landmarks - all within easy reach of major hubs like Baltimore and Washington. Soaking up the serenity of these small towns, it’s hard to believe that the city is just a short drive away. Chesapeake Bay offers the perfect place to hide from life until you’re ready to rejoin the rat race.