Weekend Getaway

A Weekend on the Upper Chesapeake Bay

Upper Chesapeake Bay

The Waters of the Upper Chesapeake may be calmer and less crowded than areas to the south, but the small history-rich communities dotting the shoreline are enjoyable stopovers during a weekend aboard.

Day 1: Havre de Grace

Concord Point Lighthouse in Havre de Grace
Concord Point Lighthouse in Havre de Grace | Credit: Chanilim714 via Wikimedia Commons

Havre de Grace would be an excellent location for a Hallmark movie. A mix of historic and charming, contemporary and quirky, the town provides an authentic Chesapeake Bay experience. Elegant inns, prime restaurants, cozy cafés, overflowing antique shops, specialty boutiques and an eclectic arts community keep the downtown vibrant with nearly non-stop activity.

Havre de Grace has several excellent museums. Waterfowl carving is at the heart of the Bay’s culture, and the Decoy Museum houses one of the finest collections of decorative and working decoys ever assembled. Explore African American history through the Havre de Grace Colored School and Cultural Center’s exhibits and displays. Open by appointment only, admission is free.

Multiple self-guided and group tours take you around town including Havre de Haunts “The Phantom Footsteps of Lafayette” tour and a seasonal tour via kayak.

Havre de Grace has an active schedule of popular annual events such as the holiday Candlelight Tour, The Ice Festival, with over 50 artistically lit ice sculptures, and the Decoy & Wildlife Art Festival featuring both vintage and modern waterfowl decoys of all types and makers. Many events, concerts and festivals are held in the 900-seat STAR Centre, the renovated Havre de Grace High School. The restored Cultural Center at the historic Opera House offers local and professional theater, concerts, films and art exhibits.

Popular with locals and visitors alike, First Fridays is a vibrant street festival held May through December. The town center is blocked off for sidewalk sales, al fresco dining, beer gardens and a live band on each of the eight blocks.

Located on the banks of the fish and fowl laden Susquehanna River, Havre de Grace has an abundance of independently owned eateries. Three coffee shops await on Washington Street, and the Vintage Café, serving breakfast and lunch, sports an old-fashioned soda fountain.

Well-known waterside restaurants such as MacGregor’s is housed in a circa 1924 bank building and Tidewater Grille offers open seating and expansive glass windows that make for spectacular sunset views. Coakley’s Pub is a casual family hang out with an extensive menu including an award- winning cream of crab soup.

Two newer entries to the dining scene are Water Street Seafood, a classy pub with a menu that includes hot steamed crabs and plump oysters, and The Vineyard Wine Bar & Bistro, which has received The Wine Spectator award for “one of the most outstanding restaurant wine lists in the world.”

For suds lovers, nano-brewers Market Street Brewery and Battery Island Brewing Company are worth a visit for the view as well as the brew.

As a Maryland-designated Arts & Entertainment District, Havre de Grace has lived up to its promise of history, culture, and outstanding food and drink.

Where to Dock: Tidewater Marina

Day 2: Havre de Grace to Chesapeake City

18 NM

A famous canal town dating back to the early 1800s, Chesapeake City is on both the National and Maryland Historic Registries and the Maryland Crab & Oyster Trail. Easily walkable streets meander around restored homes, quaint shops, waterfront eateries and charming B&Bs.

Chesapeake City Waterfront
Chesapeake City waterfront | Credit: Wayne Camlin on Flickr

Begin your day at the Bayard House for weekend brunch, then stroll through the various boutiques or explore the C&D Canal Museum. Relax over a cold craft beer at Bayheads Brewing Company while deciding which of the excellent dinner options suits your taste.

The Bayard House has a lovely canal-side sunroom for dining or an umbrella strewn Hole in the Wall deck bar for a warm evening option. Its newer sister restaurant, Prime 225, serves steak and seafood in a charming room gently lit by gas lamps.

The Chesapeake Inn Restaurant & Marina offers fine dining inside or dockside delivery along with energetic live music on the deck. Guests enjoy top- notch entertainment ranging from comedy to dance parties in the ballroom.

On the northern shore, Schaefers Canal House has convenient dockage moving in or out of the C&D Canal. A parade of yachts, ships, tugs and an occasional pirate ship pass by the multideck Lighthouse Bar where local bands liven up the evening.

Where to Dock: Chesapeake Inn Restaurant & Marina

Day 3: Chesapeake City to Delaware City

11 NM

Delaware City Fort
Delaware City | Credit: Michael Romagnoli via Wikimedia Commons

A quaint, historic seaport located at the confluence of the Delaware River and the original eastern end of the C&D Canal, Delaware City with its colorful, rich history blends easily with the spirited waterfront community.

Locals and visitors mingle at Crabby Dick’s, winner of Best of Delaware crabcakes, for crabs and a brew and a story or two. The town gets a bit crowded during the annual September Canal Fest mixing bass-heavy blues music, art in the park and an assortment of well-known artisans.

Fort Delaware, a Union fortress built in 1859 to protect Wilmington and Philadelphia ports, is accessible only by a half-mile ferry ride to Pea Patch Island in the Delaware River. Costumed interpreters enact the summer of 1864 when the fort housed prisoners of the Civil War. Well-known for being haunted, the fort has been featured on Ghost Hunters and other shows. Get in the spirit on one of the fall paranormal tours along the Prison Camp Trail.

During its entire history, Fort Delaware has never fired a shot in anger and now shares the island with The Pea Patch Heronry, one of the largest mixed species nest colonies for herons, egrets and ibis in the eastern states.

Where to Dock: Delaware City Marina is a full-service marina and boatyard with slips, fuel and ship’s store.

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