Holiday Happenings Around the Bay

Mark your calendar for a slew of festive events.

Chesapeake Bay holidays means small-town parades, high tea and wine trails, boat parades and bushel-basket trees. Where else in the world can you find yourself in Victorian England one weekend and the next celebrate on a battleship with the Grinch? Not to mention handmade crafts, boozy hot chocolate, and a Harrriet Tubman-inspired dance party. This list just scratches the surface of everything available, so look to see what’s going on near you. From the Bay to the ocean, there’s something here during the holiday season.



Mr. Paca’s Storytime at William Paca House and Garden

Tuesday December 6 • 10–11:30 a.m.

For the little ones in your life, Mr. Paca’s Garden Storytime invites children ages 3 to 7 to join them on Tuesday mornings to enjoy songs, a craft activity and reading. This session focuses on Daddy Christmas, Hanukkah Mama and My First Kwanzaa — stories about how two young girls celebrate the winter holidays.

Eastport Yacht Club Lights Parade

December 10, 2022 • 6–8 p.m.

No holiday in the sailing capital would be complete without the Eastport Yacht Club Lights Parade. Its creativity (think lighted palms, Christmas trees and snowmen) has earned the EYC event a spot on the lineup of Maryland Events of the Year. The best views of the boats are near the Eastport Bridge, the Naval Academy, City Dock and Ego Alley. Or get out on the water and take it in from the deck of Harbor Queen, a steamboat-style party ship operated by Watermark. Admission is $10 or the donation of a bag of non-perishable food for people or pets.;

Midnight Madness

Dec 1, 8 and 15 • 4–11 p.m.

For three Thursday nights in December, downtown Annapolis becomes a festive street party with specials at shops throughout town, strolling carolers in period costume, impromptu second-line parades led by Naptown Brass, and whatever else frivolity the locals can come up with.

To plan your visit, from more events to lodging, go to


Parade of Lighted Boats

December 1, 2022 • 6–8 p.m.

On land and on the water, Charm City lights up for the holidays. For the boating community, especially in December, where there’s a harbor, there’s a boat parade. The 31st Annual Parade of Lighted Boats begins at Anchorage Marina. Look for the decorated vessels anywhere from Canton and Fells Point waterfronts to Harbor East, the Inner Harbor and Federal Hill.  

Washington Monument Lighting

December 1 • 5–9 p.m.

For many of its citizens, Charm City’s holiday season officially begins with the lighting of Baltimore’s Washington Monument (not to be confused with the white marble obelisk on Washington, D.C.’s  National Mall), located in hilltop Mt. Vernon Square. Come for the fireworks, a children’s village, caroling, food vendors, a local makers’ market and music, including selections from the Morgan State University Choir.

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Cambridge Dorchester Crabby Christmas Parade
and Crab Basket Lighting

December 3 • 5 p.m.

The 73rd Annual Cambridge Dorchester Crabby Christmas Parade steps off from Long Wharf at 5 p.m. Line up along the route to enjoy this year’s version of what was once named the longest nighttime parade in the state. You’ll see talented marching bands, floats, classic cars and costumed characters as they make their way to the parade’s end at Washington Street. Stay on after Santa’s arrival and join in a Cambridge holiday tradition as the region pays homage to its watermen and women with the lighting of a 20-foot-tall tree made from bushel baskets and buoys.

Harriet’s Jazzy Holiday Ball

December 12 • 7–9 p.m.

The Harriet Tubman Museum and Educational Center invites you to dance the evening away to upbeat music at Harriet’s Jazzy Holiday Ball. The holiday merriment takes place at Heirloom Athletics in Cambridge. 

Christmas Train Garden

Weekdays, 6–9 p.m.; weekends, 1–4 p.m. and 6–9 p.m.

For train aficionados, the holiday season is a time for model displays. Since 1934, Cambridge Rescue Fire Company 39 has kept to that tradition. Their Christmas Train Garden is the longest continually operating fire department train display in the United States and remains in its original home at 307 Gay Street. Every December since 1934, the RFC has run a daily display for the community. Take up their invitation and take the train lover in your life to Cambridge and go see them all through December.

To plan your visit, go to

Chesapeake City

Holiday Sip and Shop

Sunday, December 4

If you’re looking for a day of wine tasting, libation sampling, music and shopping, the Chateau Bu-De, Broken Spoke and Crow wineries have you covered with their holiday Sip & Shop. Add in Deep Blue Restaurant at historic Kitty Knight House and it’s the perfect holiday event. Book tickets in advance, then hop on a shuttle that makes the rounds to all four venues. Each stop gets you three wine samples (or make that Boozy Hot Chocolate at Kitty Knight) and the chance to shop for handcrafted holiday gifts by local artisans. (You can also drive yourself if you just want to do the shopping.) And in any season, the view of the Bohemia River from the hilltop at Chateau Bu-De is breathtaking. The event is expected to sell out, so book in advance at any of the venue’s websites.;;;

Christmas Parade and Market 

by Poplar Hall

Saturday, Dec 10 • All day

Behold a parade of horses, holiday bagpipers, local beverages galore and the best artisans from the Upper Bay and beyond at this elaborate street party in Chesapeake City, led by the Victorian-minded owners of historic Poplar Hall in nearby Newark, Del. See why it’s been named one of the Top 50 Christmas Markets in the U.S. by Food and Wine.;

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A Dickens of a Christmas

December 2–3 • Events run all weekend

The very Victorian “A Dickens of a Christmas” returns to historic downtown Chestertown, with no evidence of Scrooge in sight. It’s a weekend of nonstop good times, sponsored by Main Street Chestertown. Make it authentic and “dress like the Dickens” (you can rent garb onsite), sing along with carolers, or go full steam ahead into the festivities and enter the Bedlam Bed Race. For a less high-spirited experience, take a carriage ride, or have a toddy around the bonfire and enjoy the sounds of the American Rogues; their repertoire covers everything from movie soundtracks to foot-stomping Irish jigs. Make sure to visit the Bank building, transformed for the weekend into London Row, for handcrafted holiday gifts created by local artisans. Take the kids to visit Santa’s house in Fountain Park, or to the Flea Circus and petting zoo. Finish off your weekend merriment with a delicious Holiday Tea and a house tour on historic Water Street near the Chester River.

To plan your visit, go to

Kent Island

Tree Lighting at Kent Narrows

December 3 • 2–6 p.m.

Join the Queen Anne’s County Waterman’s Association when their Basket Tree returns to the Kent Island waterfront, on the grounds of the Fisherman’s Inn Crab Deck. Each basket is hand-painted by local community members, honoring watermen both past and active. Come early to purchase nautical and holiday gifts crafted by local artisans; stay for the 6 p.m. lighting ceremony and join the community in honoring past and present watermen.

To plan your trip, go to

Ocean City

Winterfest of Lights

November 17–December 31

From mid-November until New Year’s Eve, Ocean City celebrates its 30th Winterfest of Lights. At Northside Park, take the walking paths through thousands of twinkling, animated displays. You’ll see Santa’s Workshop, Twelve Days of Christmas, the Candy Cane Woods, and even a nightly show put on by a 50-foot performing tree. Santa makes an appearance at the Park every night until December 23. Don’t miss the Winterfest gift shop.

To plan your visit, go to

St. Michaels

Christmas in St. Michaels

December 9–11 • Events run all weekend

According to many of its citizens, there’s no Christmas like a St. Michaels Christmas, especially when Midnight Madness takes over. It’s a weekend of late-night shopping and strolling the bright and beautifully decorated streets of downtown. No “picture-postcard town” would be complete without a holiday parade. On December 10, grab a Santa hat or full costume and take your place in the Talbot Street Parade’s Santa Dash. If you’d rather watch than walk (or run), grab a spot on the street to enjoy the lineup of llamas, boats, bands and antique cars leading up to the grand arrival of Mr. and Mrs. Santa. Later that night, head for the waterside where the parade of lighted boats returns to St. Michaels Harbor.

To plan your visit, go to

Wye Mills

Old Wye Mill Christmas Shoppe

December 3 and 17th • 10 a.m.–4 p.m.

On December 3, history and the holidays come together when the Old Wye Mill Shop opens for two Saturdays in December. Choose from pottery, ornaments, stone-ground flours and fresh-baked goods, with proceeds going to support the mill’s preservation and operations. Try the Mill’s jellies; visitors have been known to return especially for the Peach Pecan. While you’re there, take time to view the historical display and discover the workings of a mill that has ground grain since 1682.

To plan your visit, go to



Biggest Holiday Weekend

December 2–4 • Events run all weekend

Historic Alexandria charms any time of year, but never as much as around the holidays. Kick things off at 11 a.m. on the first Saturday of December with the 51st annual Scottish Christmas Walk Parade, featuring Scottish bagpipers, Scottish kilts and even Scottie dogs, dressed up for the occasion. The Holiday Boat Parade of Lights sets sail along the Potomac at 5:30 p.m., with viewing parties up and down the riverfront, including the pop-up beer garden from Port City Brewing Company. But the festivities continue all month at the shops and galleries along the historic city’s cobblestone streets.

To plan your visit, go to


Christmas by the Sea

December 3 • All day

Take an island holiday and experience Chincoteague’s Christmas by the Sea. Join the festivities on December 3 at the island’s Holiday Home tour of homes, inns and art studios. At 6 p.m., the Old-Fashioned Christmas parade lines up at Main Street. This year’s theme is “Christmas in Toyland.” View the parade of floats, marching bands, decorated boats, classic cars, equestrian teams and fire companies from all around the Eastern Shore. Meet Santa for after-parade festivities at the Chincoteague American Legion Post. Throughout the month, visit the Museum of Chincoteague’s Christmas Tree Village and vote on your favorite decorated tree. On December 31, come as you are or as your favorite costumed character for New Year’s Eve fireworks and lighted horseshoe drop. On January 1, 2023, in the home of the Saltwater Cowboys, welcome the New Year with the Polar Pony Plunge.

To plan your visit, go to


WinterFest on the Wisconsin

November 9–January 1 • Wednesday–Sunday from 4:30 p.m.

In the Tidewater city of Norfolk, the Nauticus’s WinterFest returns bigger and better with over one million lights. Explore nine new dazzling light trails that run aboard the Battleship Wisconsin and see the Mistletoe Marina and its decorated boats. Visit the Grinch, take a scavenger hunt and unlock the mystery of Santa’s Elves. If a lighted Christmas tree by the water brings out your holiday spirit, come for a Grinch-led lighting on the fantail of the Battleship Wisconsin, nightly at 7:30, 8:30 and 9:30 p.m.

To plan your visit, go to


Lights on the Lawn

Dec 10–11 • Events run all weekend

In Onancock, from December 3 to 31, experience Lights on the Lawn, the annual outdoor display of lighted Christmas trees on the grounds of Ker House, considered “the finest and most elaborate Federal mansion on Virginia’s Eastern Shore.” But for the biggest party, on Saturday, December 10, begin the day with a Holiday Artisan Market at the Historic Onancock School. Later, make your way to the Wharf to welcome Santa (and his kayak reindeer) as he arrives by boat, then take a tour of homes dressed up for the holidays. And on Sunday, December 11, join Onancock residents for a small-town Holiday Parade of floats, fire trucks and caroling.

To plan your visit, go to


Grand Illumination

December 3, 10, 17 • Step back in time to Colonial 

Williamsburg at one of three Grand Illumination weekends. Celebrations run all weekend, with the big show on Saturday night, where revelers can enjoy fireworks displays along with the weekend-long musical performances, holiday shops and period decorations throughout the Historic Area. Celebrate the Yule Log and join a holiday procession beginning at the Capitol, where you can make a wish with a sprig of greenery tossed into the bonfire. Book at table at an historic tavern for a sit-down dinner, or bring lawn chairs and partake from food trucks in the center of town.

To plan your visit, go to