Holiday Happenings Around the Bay

Christmas on the Chesapeake Bay is a magical mix of tradition, culture, and community pride—it’s oyster shell ornaments, crab basket trees, and lighted boat parades. It’s small-town celebrations, riverwalks and lighted Christmas trees, the creativity of local artisans, and the army of tireless elves who make it happen. Here’s a sample of where to go and what to see on the Bay this holiday season.

Chestertown, Maryland

What to Do

On December 2–3 the very Victorian Dickens of a Christmas returns to downtown Chestertown for its sixth year of eating, drinking, and merriment. On Friday, enjoy oysters around the bonfire with live music, including jazz with the Kent County High School Band, selections from the Garnett Elementary Chorus and River Voices, and topped off by a jam session with Dell Foxx Company. On Saturday, get ready to “Run Like the Dickens” in a 5k run from High Street to the Chestertown Rail Trail. Support your local farmer, baker, and artisan—buy produce, baked goods, and handcrafted gifts at the Farmers Market. When it’s time to get off your feet, take a carriage ride or have a beer around the bonfire. 

There’s more music and laughter on the small stage—listen to the O’McPub Band, Jimi Kinstle’s One Man Christmas Carol, and laugh out loud with Comedy by Robert Mac. At Fountain Park, Santa welcomes kids of all ages to his open house. While you’re there, take your little ones to the Stepne Station for children’s activities. Wind down the weekend’s revelry with a delicious Holiday Tea and a house tour on historic Water Street. But don’t miss the event’s epic finale with music by the Baltimore Pipe Band and American Rogues.

Where to Shop

While you’re in town, take time to visit Chestertown RiverArts during its annual Holiday Show and Sale that runs through December 24. It’s time well spent, the one-of-a-kind handmade selections include ornaments, wreaths, fine art, ceramic, pottery and photography.

There’s always good eating in Chestertown—from soul food to seafood, fine dining, wine, sushi, and tapas, it’s a small town with big tastes.

Where to Stay

There are literally dozens of charming historic inns and B&Bs to accommodate you in and around Chestertown, like the White Swan Tavern, which has been a familiar landmark in Chestertown since its pre-Revolutionary War days. Conveniently located in the center of downtown Chestertown, within walking distance of the shops and restaurants, the Chester River waterfront, and the weekly Saturday farmer’s market, the White Swan offers—just as it has since the 18th century—“a comfortable… Public House… with every attention given to render comfort and pleasure to such as favor it with their patronage.”

Oxford, Maryland

What to Do

For Oxford, often called the prettiest tiny town on the Chesapeake, size doesn’t matter when it comes to grand holiday celebrations. From December 1–3, the historic port town pulls out all the stops for Christmas on the Creek, Oxford’s unique celebration of the most wonderful time of year.

Get your wish list ready and start the weekend outside Friday Vintage Treasures and Trade, where an oversized mailbox will delight children mailing their letters to Santa. Just before sunset on Saturday, make your way to the town park to await Santa’s arrival on a fire truck. There’ll be cookies, caroling, and lots of good cheer when he arrives to light the town’s Christmas tree. In front of Pope’s Tavern, watch Christmas on the Creek come to life in a simultaneous spectacular display of Christmas colors when lights on the town dock and more than 60 private docks light up the town all at once.

Where to Shop

Festive holiday weekends call for shopping. Pick up a one-of-a-kind gift for someone (or yourself) at one of the town’s unique shops. Along the way, you just might find hot chocolate, gift baskets, and raffles to sweeten your efforts. At Vintage Treasures and Trade, discover a huge collection of antiques, furniture, classic designer wear, jewelry, and artwork. Visit the Treasure Chest for art and gifts related to the Eastern Shore and the Chesapeake Bay. Browse the collection at Mystery Loves Company, the full-service bookstore specializing in mysteries, books with nautical and Eastern Shore themes, those written by local authors, and gift items. 

Grab some carryout at the Oxford Deli for homemade salads, soups, and sandwiches. Homemade pies and a wine tasting are rumored to be in the works for that weekend. For coffee and pastries, check out the Oxford Cafe. Or if a sit-down dining experience is more to your liking, visit Pope’s Tavern and Anthony’s for authentic homemade pasta and Italian cuisine. At the historic Robert Morris Inn, enjoy breakfast, lunch, or dinner. Capsize, located on Town Creek, is open for the season with a brand-new steakhouse menu. At Doc’s Sunset Grill, enjoy casual cuisine with a spectacular view of the Tred Avon. Even in winter, Oxford is a pretty town.

Photo by John Santic

Solomons, Maryland

What to Do

If waterside celebrations appeal to your sense of holiday spirit, spend a day (or a weekend) in Solomons, where the Patuxent River meets the Chesapeake Bay. On December 9, the town lights up for A Nautical Christmas, the theme of its 42nd annual Christmas Walk and the island’s boat parade. 

Stroll along the RiverWalk, lit with thousands of white lights, and stop by the gazebo to offer Merry Christmas greetings to Santa. Watch the parade of more than 30 decorated sail and powerboats as they make their way up to Back Creek, around the island, and back to the RiverWalk.

Where to Shop

Although Solomons has more restaurants than shops, on Dec. 9 a one-day village of more than 30 vendors joins the town’s year-round boutiques and stores near the parking lot of the Tiki Bar and Grill. Visit the village and the brick-and-mortar businesses. Browse The Blue Shell for candles, fashion accessories, and home fragrances, or the Equinox for products for the mind, body, and spirit. Shop Carmen’s Galley for art, jewelry, handmade pottery, and sculptures. At Grandmother’s Antiques, shop for ornaments, collectibles, and that one item that brings back memories of years gone by. If you or someone you know loves marine life, fossils, and the history of the Patuxent and the Chesapeake Bay, visit the Calvert Marine Museum and Gift Shop.

With 11 restaurants in Solomons, there’s an eating establishment to satisfy almost any food craving—from ribs and seafood to Italian, sushi, and many selections in between. Walk around town and see what appeals to your tastebuds.

Where to Stay

In case another day or two in Solomons is warranted, book a stay on the waterfront at the Solomons Victorian Inn, the Back Creek Inn, or the Blue Heron Bed and Breakfast.

Photo by Pat Venturino

Havre de Grace, Maryland

What to Do

Magical properly describes the transformation of Havre de Grace into a holiday wonderland—the thousands of lights, the lighthouse decorated with red ribbon next to an illuminated 25-foot Christmas tree, and lighted boats that have come to dock year-round on the river. Start your Christmas fun on Friday, December 1 with the Holly Jolly Christmas Parade, a festive procession of floats and entertainment that ends with a tree lit by Santa Claus and the Mayor of Havre de Grace. If you’re a music lover, the town’s Star Center hosts a Nat King Cole tribute on December 9, a Big Band tribute on December 10, and a Carpenters Tribute Christmas show on December 16.

On December 8 and 16 bring the kids to Santa Land for story time, cookies and hot chocolate, then take a horse-drawn carriage around town. Havre de Grace prides itself on its eclectic collection of shops and local businesses. On those two two days, the stores stay stay open late; if you’re looking for unique gifts, browse the shops for original art, antiques, crystals, clothing, books, turntables, and vinyl. And in this, the “decoy capital of the world,” don’t forget to explore the selection of decorative carvings.

Where to Shop

As much as Havre de Grace prides itself on its one-of-a-kind shops, the same holds true for its independently owned eating establishments. Rather than one, the town recommends them all. From restaurants serving Cajun fare to waterfront dining, seafood, burgers, and retro breakfasts, there’s something for every taste in town.

Where to Stay

Great Wolf Lodge
Perryville, Maryland

For an immersive holiday experience with lots of wintertime fun, reserve a space for your “pack” at Great Wolf Lodge. Inside the Globes at Snowland, you’ll enjoy your own private winter wonderland. There’ll be hot cocoa, cookie-making, and games. Try your hand at Snowland Bingo and Trivia, or test your skills at ring toss or a scavenger hunt. With yoga, discover your flexibility or try out your best moves at the Frosty Fest Family Dance Party. When Santa arrives, reveal your Christmas wish to the Big Man or drop it in the Letters to Santa mailbox for him to read later.

Enjoy Snowland, but don’t forget the Waterpark at Great Wolf Lodge. For toddlers to adults, the park has passes, trails, coves, and activities to discover and explore. And there’s no winter unless you want it – the temperature of the indoor water park is kept at a warm 84 degrees all year long.

Mount Vernon, Virginia

What to Do

Time travel to an 18th-century Christmas at George Washington’s Mount Vernon. Nestled along the Potomac River, the first president’s former home offers plenty of activities for all ages. On November 24–25 and December 1–2, 8–9 and 17, a candlelight tour will be available of the mansion’s interior and grounds. A dazzling fireworks show will be held here as well on December 15 and 16. 

The estate will also host Aladdin the Camel from November 26 to January 6. The animal pays homage to a camel who reportedly visited the property in 1787. On select days, other holiday activities will take place, including chocolate-making demonstrations, holiday fifing and kids’ winter crafts. Be sure to stop by Half Crown Bakery during your trip for some scrumptious gingerbread.

Another intriguing destination is the Pope-Leighey House. Built by famed architect Frank Lloyd Wright, the house showcases stunning examples of mid-century architecture and decor. On December 1–2, 8–9 and 15–16, nighttime holiday tours will be held. Tickets are needed and can be bought in advance. 

Where to Shop

Don’t miss the Shops at Mount Vernon, where you’ll find a wide spectrum of distinctive items ranging from heirloom seeds (most collected from the estate’s gardens) to porcelain ornaments, and plenty more. Many exclusive products are also available, like freshly milled cornmeal from the estate’s gristmill and hand-forged blacksmith nails made on-site. 

Where to Stay

Hampton Inn & Suites Fort Belvoir Alexandria South is one of the closest accommodations to the historic estate. The contemporary hotel offers free parking and breakfast. Hotel Indigo is a 20-minute drive away, but the charming nautical-themed hotel is well worth the trip. Located in Old Town Alexandria, it has views of the Potomac River and an illuminated patio where guests can enjoy a warm evening drink. 

Colonial Beach, Virginia

What to Do

Colonial Beach is quiet seaside town famous for its rich history and iconic 19th-century architecture, though it’s an overlooked holiday destination. To kick off the season, a lighted boat parade will set sail at dusk on November 25. The decorated vessels will float down the bordering Potomac River to Monroe Bay. 

On December 2, Santa’s Wonderland & Winter Festival Parade will be held from 12:30–5 p.m. in Town Hill. Apart from the parade, the park will have fire pits, food and gift vendors and Santa photoshoot opportunities. 

Where to Shop

For wine connoisseurs, a stop at Monroe Bay Winery is a must. Established along Monroe Bay, delectable wines and hard apple ciders are available for purchase. For the shoppers, Peddlers Market contains over 90 small boutiques that house everything from antique books to fine art. 

Hawthorne Mercantile has a variety of goods that will make perfect gifts, including stylish clothing, candles, toys and coffee mugs. 

Where to Stay

Situated within a 1905 Victorian Home, Tides Inn Bed & Breakfast has four spacious suites and one bedroom. Weekend stays include a delicious breakfast from its Tides Inn Market. 

Riverview Inn will transport you to the 1950s with its retro ambiance. The building (hard to miss with its flashy turquoise and red exterior) is a short walk from the beach and nearby restaurants. 

Onanacock, Virginia

What to Do

For a laid-back holiday getaway, Onanacock is the place to be. The small coastal town is rich in culture and is a great spot for wildlife viewing and boating year-round. Its charm becomes especially vibrant during the holidays with its numerous festivities. 

On December 9, a holiday home tour will take place. From 1–5 p.m., guests can explore a handful of local residences to appreciate their unique architecture and interior design alongside holiday decor. 

Christmas at Cokesbury will feature the Orchestra of the Eastern Shore on December 9 at 2 p.m. Hosted at Cokesbury Church, listeners will be treated to a melange of carols and Handel’s Hallelujah Chorus. 

Where to Shop

Onanacock is packed with small businesses. One is the Red Queen Gallery. Filled with paintings, sculptures, pottery and soaps, the store is a charming place to browse. 

Founded in 1953, C.D. Marsh Jewelers designs handcrafted jewelry, and is best known for making customizable Chesapeake Bay Bracelets, which come in sterling silver, 10K gold or 14K gold options.  

The Holiday Artisan Market at Historic Onanacock School will take place December 9 from 10 a.m. to 3 p.m. Visitors can tour resident art studios (once old classrooms) and additional vendors in the Main Gallery in search of distinctive holiday gifts. 

Where to Stay

Constructed in 1907, the Charlotte is an elegant oasis featuring eight beautifully decorated rooms. This cozy boutique hotel also has a restaurant and bar. 

As the town’s first bed and breakfast, The Spinning Wheel is a quaint stay that’s also a certified green lodging. There is one pet-friendly room and amenities include breakfast, evening drinks and bicycles. 

Virginia Beach

What to Do

While it might be a lively summer destination, Virginia Beach still flourishes during the winter. 

Starting November 16 at 5:30 p.m., the city’s boardwalk transforms into a holiday light extravaganza. Cars can drive down the boardwalk through lighted archways to view quirky light formations (many of which are nautical-themed) while listening to a specially synchronized holiday music radio channel. Tickets are required. 

On December 10, head to Mount Trashmore Park for Chabad’s annual giant menorah lighting. The public celebration will last from 4:30–6 p.m. and include plenty of other festive fun, like music and fresh latkes. 

To escape the chilly ocean breezes, stop by Sandler Center for the Performing Arts to enjoy numerous seasonal performances, including NUTCRACKER! Magical Christmas Ballet!, A Classical Christmas, and Vienna Boys Choir–Christmas in Vienna. 

Where to Shop

The Virginia Beach Christmas Market, held November 24–26 at the Virginia Beach Convention Center, will feature over 175 vendors selling items such as nature photographs, pet holiday outfits and mouthwatering confections.

The Shops at Hilltop is home to many well-known brands alongside some local favorites. The mall also provides horse-drawn carriage rides for shoppers to enjoy.

To load up on holiday decor, stop by Christmas Mouse, where hundreds of interesting ornaments are for sale. There are also rare collectibles, like Byers’ Choice Christmas Carolers and Jim Shore figurines. 

Where to Stay

Historic Cavalier Hotel & Beach Club is a regional gem. First opened in the 1920s, the restored Jazz Age hotel is a luxurious oasis with many rooms having Atlantic Ocean views. Guests can enjoy a meal in one of its restaurants or stop by its in-house bourbon distillery for a tour or tasting.

Barclay Cottage Bed and Breakfast is one of the oldest lodgings in the area. Designed with a tranquil maritime vibe, the bed and breakfast is two blocks from the oceanfront and provides guests with a two-course breakfast during their stay. There’s even an on-site spa. 

George Washington’s Egg Nog
This is a riff on a traditional recipe for a holiday treat like one Washington enjoyed serving his many guests at Mt. Vernon, incorporating the rye whiskey he distilled on his plantation. 

1 qt. whipping cream
1 qt. milk
12 eggs, separated
½ cup sugar 
1 pt. brandy 
½ pint rye whiskey
½ pint Jamaica rum
¼ pint sherry 

•          Mix all the liquor in a large bowl
•          Separate yolks and whites of 12 eggs
•          Add sugar to the yolks, beat well
•          Add milk and cream, beating gently 
•          Beat egg whites until stiff and fold slowly into the cream mixture 
•          Blend the egg and cream mixture into the liquor bowl 
•          Let set in cool place for several days
•          Serve chilled, sprinkled with freshly ground nutmeg.

The original recipe includes the instruction to “taste frequently,” as we’re certain George would have done. After all, the one tooth that wasn’t wooden was a sweet one! Happy holidays! 

Niambi Davis was raised on the Eastern Shore of Maryland and takes every opportunity to share her love of the Land of Pleasant Living through words and pictures.

Rachel Kester is a Virginia-based freelance writer who covers topics ranging from the environment to culture.