Between boat parades, colorful displays, and after-hours shopping strolls, the Chesapeake Bay region lights up at holiday time—literally! There’s something for everyone, whether your light shines from Christmas candles, a Hanukkah menorah, a Kwanzaa kinara, or anything else. Here are some of our favorite events around the Bay. Go for the day or make a weekend of it, and fill out your gift list along the way.
Note: As with everything during COVID-19, events may go on as planned, or they may be canceled out of caution. Look for the latest updates on the town and event websites and social media before heading out.
Alexandria, Virginia
Celebrate
Old Town Alexandria was established in 1749 by Scottish merchants, who are celebrated every year in the Scottish Christmas Walk, typically held first weekend of December. The parade takes place rain or shine, with tartan-clad marchers representing dozens of clans parading through Old Town, accompanied by fife and drum bands, classic cars, even trotting Scottie dogs. The parade ends with a concert at Market Square, and proceeds benefit the Campagna Center.
Head to the Alexandria Lyceum on Nov. 28 for the Grand Chanukah Menorah Lighting, a festive night of music, hot treats (including potato latkes and donuts), and dreidel giveaways. At the Holiday Boat Parade of Lights, bedecked watercraft cruise along a one-mile stretch of the Potomac while onlookers peruse the vendors along the waterfront. Step back in time with candlelight, 18th-century music, and fireworks displays at Christmas at Mount Vernon. Visitalexandriava.com/holidays
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Red Barn Mercantile has a beautifully curated selection of home goods, puzzles, you name it, including Virginia-inspired gifts. Pop down the block to sister shop Penny Post for cards and stationery. On the waterfront, the Torpedo Factory Art Center is home to the largest collection of accessible working studios in the U.S., with fine-art paintings, photography, blown glass, jewelry, and more, on sale from the artists. The Old Town Shop shares local pride via cute housewares, logo shirts, and artisanal crafts and food in Locals Alley. Look to the Historic Alexandria Museums (including its Black History Museum and the Stabler-Leadbeater Apothecary Museum) for unique finds.
Stay
Stay in the heart of it all at The Alexandrian, located right on King Street. This Autograph Collection hotel has 241 guest rooms and a special secret: an open-air atrium garden at King & Rye restaurant, which gets transformed into a Winter Wonderland every season, complete with heated igloos. (Reservations strongly recommended.) Thealexandrian.com
Richmond, Virginia
Celebrate
Lights, lights, and more lights—it’s a theme in RVA, and there are so many ways to soak up the sparkle. The Dominion Energy GardenFest of Lights turns Lewis Ginter Botanical Garden into a visual feast for all ages, with twinkling displays, model train sets, a cozy fire for s’mores and hot cocoa, and even pet-friendly walks on select evenings. It opens in mid-November and runs through the New Year.
If you think more is more, and even more is even better, you’ll love the Tacky Lights List, an unofficial tour of the brightest, gaudiest, most over-the-top homemade displays around the city. Get the scoop on participating homes from The Richmond-Times Dispatch, VentureRichmond.com or the Tacky Lights Richmond Facebook page.
The Ẹlẹgba Folklore Society started the Capital City Kwanzaa Festival in 1990, and it has grown into one of the largest on the East Coast. It celebrates the holiday’s seven guiding principles—which include unity, faith and self-determination—via music, dance and spoken word, both in person and online. Visitrichmondva.com
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RVA is known for its thriving creative entrepreneurs, making it the perfect place for unique shopping. In the Arts District, bespoke custom clothier Ledbury recently expanded into shoes, offering European-style craftsmanship and tailoring, all made in Virginia. Sassy Jones was a winner of HSN’s The Big Find, thanks to her colorful bags, jewelry, and accessories. Awl Snap’s smart leather bags and clutches are all handmade onsite. The Someday Shop has well-curated home goods, including reclaimed furniture and vintage French copper pots that would brighten up any kitchen.
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The grande dame of Richmond hotels, the circa-1895 Jefferson Hotel goes all out for the holidays, with garland-wrapped, wrought-iron balconies; hundreds of live poinsettias; an elaborate gingerbread house display; and 20+ trees, including the signature 30-foot beauty in the Rotunda, a two-story atrium with a stained-glass ceiling. Holiday afternoon tea is served on the mezzanine overlooking the tree, while overnight guests can reserve a table with that prize view for cocktails and light snacks, available on select nights. Jeffersonhotel.com
Annapolis, Maryland
Celebrate
Maryland’s state capital is even more of a beauty at the holidays, with wreaths, ribbons, and greenery decorating the lampposts and windows along its cobblestoned Main Street, and a huge lit-up tree and menorah at City Dock Park. It’s the perfect background for Midnight Madness, held on three consecutive Thursday nights, when shops stay open late, and entertainment comes via live music, strolling carolers, and impromptu photo ops in Snowflake Alley. Watermark Tours offers candelight walking tours, or you can take in the decorated homes along Spa Creek via a Jolly Express boat ride on Miss Anne, complete with hot cocoa and blankets to keep you warm. On Dec. 11, the Eastport Yacht Club’s Lights Parade brings viewers to every restaurant, sidewalk, and dock within viewing distance of Spa Creek. Head to Sandy Point State Park, at the foot of the Bay Bridge, for Lights on the Bay. This annual light show runs from late November through the new year, with 70+ elaborate seasonal displays from reindeers to schooners, set up along a two-mile driving route through the park. Visitannapolis.com
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Local by Design on Main Street showcases the work of local artists and makers, from ornaments and wall plaques to seriously fine art. The Historic Annapolis Museum Gift Shop always intrigues, and don’t miss a stroll down perfectly quaint Maryland Avenue, where you’ll find well-curated collectibles and antiques at Evergreen, sustainable clothing and home goods at Cupla, and the sweetest bookstore you ever saw at Old Fox Books and Coffee. You can also pick up a bottle of Irish eggnog at Galway Bay.
Stay
Check into the heart of town at The Annapolis Waterfront Hotel, where a balcony guestroom gives you a view of the harbor lights. Half a block from City Dock, the stately Flag House Inn has five gorgeous rooms, stellar breakfasts, and that most magical gift in Annapolis: free parking. Or skip the crowds at the cozy Inn at Horn Point, located across the bridge in Eastport. Annapoliswaterfront.com; Flaghouseinn.com; innathornpoint.com
Williamsburg, Virginia
Celebrate
Party like its 1699 in Virginia’s Colonial centerpiece, where holiday events offer a glimpse of festivities past, with traditional décor, music, and strolling carolers. Colonial Williamsburg’s signature Grand Illumination runs over three weekends in December. Friday is the procession of the Yule Log, while Saturday evenings offer a holiday play and a visit by Father Christmas, ending in fireworks.
“Christmastide in Virginia” at Jamestown Settlement gives a different glimpse of holidays past, using living history reenactments to show how holidays may have been celebrated in the earliest days of the English colony.
For something more contemporary, the first weekend in December brings Yorktown’s Christmas Market, with almost 100 vendors setting up stalls on Main Street that sell crafts, art, and gifts galore. The following weekend’s Mistletoe Market focuses on food vendors, with cakes, cookies, and other sweet treats. Nearby Busch Gardens puts on one of the largest holiday displays in North America, a spectacle of 10 million lights, Radio City Music-style stage shows, and dozens of vendors selling food, drinks, handmade gifts, and more. New this year is a corn maze, only made with Christmas trees. Colonialwilliamsburg.org; visityorktown.org; buschgardens.com/williamsburg
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Merchants Square is a great one-stop shopping destination. New to the square is Brick & Vine. This flagship store of the Shops at Colonial Williamsburg, combines three of their stores under one roof, with period-influenced housewares, specialty food and wine, and seasonal décor destined to become keepsakes. Opened in 1938, Williamsburg Pottery is almost as famous as the museum. Salt-glaze pottery is still made onsite, sold alongside a dizzying array of kitchenware, home décor, local wine and craft beers…the list goes on and on. J. Fenton is home to gorgeous handmade quilts, comfy linen tunics and dresses, jewelry, and unique housewares.
Stay
The Williamsburg Inn is stunning this time of year, when strings of white lights cover every column, balcony, and tree in sight. Holiday packages include museum admission, daily breakfast, retail shopping pass (with discounts), and a keepsake ornament. Make it even more special with a traditional afternoon tea, paired with a seasonal-themed loose-leaf tea and pastries, or prix-fix holiday feasts. Colonialwilliamsburghotels.com
Baltimore, Maryland
Celebrate
Charm City goes all out for the holidays. On the first night of Hanukkah, gather for the lighting of the 30-foot menorah at McKeldin Square, followed by a feast of latkes, jelly doughnuts, and live music. At the 50th anniversary lighting of the Washington Monument in Mount Vernon, held Dec. 2, expect carolers, food and drink vendors, and even fireworks. On December 5, the annual Mayor’s Christmas Parade brings more than 100 marching bands, plus uniformed first responders, revving Harley Davidsons, festively clad Mummers from Philly, a steam calliope, and local celebrities waving from floats. Get a taste of the Old World by sipping gluhwein and nibbling gingerbread as you peruse the German Christmas Market, which takes over the Inner Harbor’s West Shore Park every weekend in December. Storytelling, gift-making and workshops bring the seven-day festival of Kwanzaa to life at the Reginald F. Lewis Museum. Kids will love The Polar Express Train Ride at the B&O Railroad Museum, and the creative animal displays at Zoo Lights at the Maryland Zoo, available as a walk-through or drive-through experience through the new year. And a holiday just isn’t a holiday, hon, without experiencing the over-the-top light show on 34th Street in Hampden, nicknamed the Miracle on 34th Street. Homes on the block go all out, drawing up to 1,000 visitors a night. baltimore.org/events
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Baltimore is a city of neighborhoods, and shopping is a great way to experience the flavors of each. Hampden is home to the city’s top indie bookstore, Atomic Books, and a great spot for vintage and collectibles. At Harbor East, an open-air mall overlooking the harbor, you’ll find popular Charm City Run and the flagship Under Armour store, which carries only-in-Baltimore merch. In Fells Point, pick up trendy teenwear at Brightside Boutique, shoes and bags at Poppy & Stella, and new and used vinyl at The Sound Garden—and hit historic pubs and Broadway Market along the way. Keep an eye peeled for holiday pop-ups like Made in Baltimore, now in its 7th year.
Stay
Four Seasons Baltimore transforms its rooftop garden into a Winter Village, complete with music, fire pits, and a skating rink overlooking the harbor. In Fells Point, Sagamore Pendry’s open-air courtyard comes alive with lights and greenery, mulled wine and s’mores around the fire pits, and holiday shopping pop-ups. The Ivy in Mount Vernon is a must for its elaborate Gingerbread display. fourseasons.com/baltimore; pendry.com/baltimore; theivybaltimore.com
Rock Hall, Maryland
Celebrate
This favorite port of call offers small-town charm any time of year. At Hometown Christmas, enjoy a carriage ride through downtown, then hit the shops for holiday specials. In an Eastern Shore twist, Santa arrives by boat, then parades down Main Street for the lighting of the Crab Basket Tree—actually a series of trees, made from hand-painted baskets in an effort that raises money for community activities. Kentcounty.com/events
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The colorful cottages that make up Rock Hall Village Shops make it a pleasure to stroll, even if it’s a short way. Stock up on seasonal décor at Eastern Shore Wreath Co., and pop into The Hickory Stick for gift ideas like a Chesapeake Bay chart map blanket or Old Bay enamelware salad bowls, perfect for boat picnics.
Stay
Overlooking the protected anchorage, Osprey Point has an acclaimed restaurant along with a seven-room traditional inn, neighboring modern all-suite Annex, and a four-bedroom exclusive-use farmhouse—plus marina slips if you come by boat. Ospreypoint.com
Chesapeake City, Maryland
Celebrate
This tidy town on the Upper Bay has a key place in Bay history, overlooking the C&D Canal. Come early for its first-ever Parade of Horses, scheduled for December 4, which celebrates the town’s deep equestrian roots via dressage, fox hunting troupes, police horses, carriages, and more. The hooves hit the pavement at 9 am, and the day-long Poplar Hall Christmas Market follows, with crafts and food vendors along the waterfront. The following weekend brings the Candlelight House Tour, or stroll the Victorian village and take in the charm on your own. Chesapeakecity.com
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Try Second Spring Naturals for yummy soaps and scrubs, Mercantile at Back Creek for home decor, inluding painted furniture and custom tints, and My Jewelry Place for handmade jewelry from around the world.
Stay
Share a holiday toast at the rum-centric Rummer Lounge, which is located inside the Inn at the Canal. Then head upstairs and tuck into one of seven uniquely decorated guest rooms at this favorite B&B, set in an 1870s former merchant’s home overlooking the C&D Canal. Innatthecanal.com
Cape Charles, Virginia
Celebrate
The southern tip of ESVA kicks off four weeks of Festive Fridays in late November. Shops stay open until 8 p.m., with caroling, carriage rides, and kid-friendly activities along Mason Ave. and Strawberry St. Head down to the waterfront on Dec. 4 for the annual Lighted Boat Parade, where spectacularly lighted watercraft cruise along the mile-long waterfront, followed by an after party at Oyster Farm at Kings Creek, complete with live music. capecharlesvirginiascape.com/events
Shop
Gull Hummock Gourmet Market has the perfect host and hostess gifts, including local Chatham Vineyards wine, handmade chocolates, cheeses, artisanal honey, and more. Peach Street Books, set in a former gas station, has a great local authors section alongside new and gently used books. The Boardwalk is home to fun décor items like latchhook pillows, cocktail napkins, and fish-shaped wine racks. Cape Charles Distillery uses Virginia-grown corn and grains in their bourbon, whiskeys, and vodka, with a raw bar and craft cocktails to enjoy while shopping.
Stay
Bay Haven Inn is cozy, welcoming, and just steps from everything in town. Choose from four guest rooms, each uniquely appointed and named after a family member of the Wilson family, who built the house in 1906. Current owners Tammy and Jim Holloway make it feel like home away from home. Or spread out in one of the residences at Bay Creek Resort, which come with two to five bedrooms, full kitchens, and access to the resort’s amenities. bayhaveninnbnb.com; baycreekresort.com
Berlin, Maryland
Celebrate
Victorian Christmas is a month-long celebration in this artsy town just six miles from the Atlantic. Things kick off Thanksgiving weekend with Ice Ice Berlin, a display of three-foot-tall seasonal ice carvings that lead up to the tree lighting outside the historic Atlantic Hotel. The following weekend, marching bands, themed floats, and revelers parade down Main Street in the 50th annual Christmas Parade, capped by an appearance from Santa. In the Festival of Trees, downtown businesses decorate and display trees, then sell them by silent auction to benefit Atlantic General Hospital. Berlinmainstreet.com
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This picture-perfect town is known for its antique shops, including Victorian Charm, Stuarts’ Antiques and Town Center Antiques, and Uptown Emporium, all clustered around the town center. You’ll find the town’s thriving indie vibe showcased at well-curated shops like The Greyhound Indie Bookstore and Gallery, Harvest Guitar Shop, and East & Main Shore Supply, a great spot for beach wear, mens’ grooming goods, and quirky gifts.
Stay
One of Berlin’s oldest homes is also its newest inn. Located within easy walking distance of downtown, an 1835 farmhouse (the former Waystead Inn) has been reborn as the Inn Berlin, a chic, five-bedroom B&B with touches like organic cotton linens, HD Smart TVs, and on-request extras like custom charcuterie boards or guided tours through town. Theinnberlin.com
Urbanna, Virginia
Celebrate
The Urbanna Christmas parade is a slice of small-town Americana, with homemade floats, classic cars, and an appearance from you know who. This evening event is held on the first Friday in December, and departs from the Fire House to kick off the holiday season. Another great thing about holidays here? Oysters are at their peak, so bring your appetite! Urbanna.com/events
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Pop into Low Tide, a “coastal lifestyle boutique” on Virginia Street for cute dresses, jewelry, and accessories, Southern Tide shirts and boxers for men, and gifts like cocktail mixers. Just across the river in Irvington, find more cute womenswear at The Dandelion, crab-logoed everything at Jimmy and Sook, and statement sculptures, paintings, and jewelry at Objects and More.
Stay
You can’t help but smile walking through the reborn Chesapeake Inn. New owners Gari Lister and Matt Gobush completely redid the boutique hotel during the pandemic, creating a modern-eclectic vibe with 13 rooms, friendly extras like loaner surrey carriages and kayaks, a great onsite restaurant, and an infectious love for everything about the town. Some of the rooms allow four-legged guests, too. Thechesapeakeinn.com
Norfolk, Virginia
Celebrate
There is literally nothing like WinterFest on the Wisconsin, at Nauticus. The entire battleship becomes a lighted display, complete with talking gingerbread men, Santa’s North Pole, and holiday drinks at the new Griswold Café. (Speaking of, they’ve applied for a Guinness world record for most lights on a battleship.) ZooLumination at the Norfolk Zoo features gigantic inflatable animal sculptures by day, and a drive-thru light up experience at night. The Million Bulb Walk at Norfolk Botanical Garden is back with new light displays along the mile-long route, and new light displays. The trio of events run from mid-November through the new year. Visitnorfolk.com
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Hamilton Perkins creates backpacks, crossbodies, duffles, and more from sustainable/recycled materials, available at his downtown shop. Over on Colley Avenue in Ghent, more than 100 regional artists and artisans sell their wares at Kitsch Handmade and Vintage. Le Marché is a must for every sort of houseware, from handpainted china to crystal chandeliers. A. Dodson’s is a great spot for holiday-themed gifts, sports gifts, tech gifts, funny gifts—basically, everyone on your list. Plentiful stalls and a gigantic Yule Log bonfire take center stage at the Holiday Marketplace on the downtown waterfront.
Stay
Take in the views of the Elizabeth River from the Main Hotel, where the 23rd-floor rooftop terrace serves up small bites, craft beers, and cocktails, with fire pits to keep you toasty. More views are found in guestrooms and the indoor pool, and the downtown location makes it convenient to just about everything. Themainnorfolk.com
St. Michaels, Maryland
Celebrate
“Christmas in St Michaels” celebrates its 35th year in 2021, with a slew of events that raise money for local charities including Habitat for Humanity, Christ Church Food Pantry, Bay Hundred Community Volunteers, and educational efforts. The Talbot Street Parade is the Eastern Shore’s largest holiday parade, with marching bands, antique cars and boats, fire trucks, horses, and more. Get there early to join the Santa Dash, where red-and-white clad participants run or walk the one-mile route before the big shebang. That evening, watch the Lighted Boat Parade cruise through the harbor, or tour around on your own to see the beautiful displays on homes and businesses throughout the town. Christmasinstmichaels.org
Shop
Downtown is packed with wonderful shops, many of them tucked into Victorian-era buildings that make browsing a pleasure. Pemberton Pharmacy & Gifts is an old-fashioned drug store-meets-gift shop, with a great selection of gifts from housewares to soaps, bags, and toys. Ophiuroidea, aka “The O,” is a well-curated, catch-all boutique that reflects the Eastern Shore in décor and clothing, some of it locally made. Iron Will & Woodworks and sister shop, Reclaimed, are a treat for the eyes; owners Mark and Tracy Miller scour the country for salvage materials and antiques from neon to gas pumps, which they restore and/or repurpose into custom furniture, light fixtures, and more. Nancy Hammond’s colorful prints and paintings will cheer up any room, while Guilford & Company’s beautifully curated collection of antique and estate jewelry is a star in the mid-Atlantic. Chesapeake Bay Maritime Museum’s gift store is a must for regional books and artwork.
Stay
St. Michaels’ newest hotel is the Wildset, a 34-room boutique hotel spread across four 19th-century buildings on the north end of Talbot Street. Each room is unique, some with perks like gas fireplaces, soaking tubs, and private balconies. Or spread out at Inn at Perry Cabin, the Eastern Shore’s preeminent luxury stay. For winter, it has added private waterfront greenhouses, ideal for romantic private dinners to get a respite from holiday stress. Thewildset.com; Innatperrycabin.com
