There’s no place quite like Annapolis and the surrounding region during the holiday season. From twinkling light displays to waterfront parades, this time of year brings out the best of our community charm. Whether you’re looking to shop local, take in the lights, or spend time with loved ones, here are some of the most festive holiday events happening in Annapolis, Anne Arundel County, and the greater Washington, DC area this year.
Holiday Events in Annapolis & Anne Arundel County
Midnight Madness
Dates: December 4, 11, and 18
Location: Downtown Annapolis
Downtown Annapolis comes alive during Midnight Madness. Stroll along Main Street, West Street, Maryland Avenue, State Circle, Market Space, and Dock Street from 4 PM until midnight to shop, dine, and enjoy festive entertainment. Many shops offer refreshments, sales, and extended hours, perfect for finishing your holiday shopping while supporting local businesses.
Lights on the Bay
Dates: November 23 to January 1
Location: Sandy Point State Park, Annapolis
This beloved drive-through light display transforms Sandy Point State Park into a glowing wonderland, with proceeds benefiting the SPCA of Anne Arundel County. Enjoy sparkling light scenes along the Chesapeake Bay with family, friends, and even your pets. For a unique experience, join the special Lights & Leashes walking nights on November 21 and 22.
Eastport Yacht Club Lights Parade
Date: December 13
Location: Downtown Annapolis Waterfront
A cherished Annapolis tradition, the Eastport Yacht Club Lights Parade features boats decked out in dazzling holiday lights cruising along the harbor. Find a cozy spot along the waterfront and take in the magic of the illuminated parade.
Military Bowl
Date: December 27
Location: Navy-Marine Corps Memorial Stadium, Annapolis
The Go Bowling Military Bowl is a post-season college football game showcasing teams from the ACC and AAC. The event benefits the Military Bowl Foundation, which supports service members and their families through initiatives like Patriot Point, a retreat for recovering veterans on Maryland’s Eastern Shore.
Annapolis Holiday Market
Dates: December 13 to 21
Location: St. John’s College, Annapolis
This festive market features over 100 artisans, specialty food vendors, and live entertainment. It’s the perfect place to shop handmade gifts and local goods while soaking in the holiday spirit.
Holiday Train Display at Homestead Gardens
Dates: November 1 to December 31
Locations: Davidsonville & Severna Park
Homestead Gardens’ annual train display delights visitors of all ages with intricate model trains weaving through miniature winter villages. It’s a must-see stop for families and a beloved local holiday tradition.
Holiday Events in the Washington, DC Area
Downtown Holiday Market
Dates: November 21 to December 23
Location: F Street NW, Washington, DC
The DC Holiday Market features more than 100 vendors, live entertainment, and a festive atmosphere where even four-legged friends are welcome. From handmade crafts to gourmet treats, it’s a perfect place to find one-of-a-kind gifts.
Holiday Boat Parade at The Wharf
Date: December 6
Location: The Wharf, Washington, DC
Experience the beauty of more than 60 illuminated boats gliding along the Washington Channel. The celebration continues on land with fireworks, hot drinks, live music, and family-friendly fun, including photos with Santa and holiday karaoke.
Georgetown Jingle
Date: December 6
Location: Throughout Georgetown
Enjoy live music performances across Georgetown featuring local artists playing festive favorites in every genre, from jazz and pop to a cappella and kids’ music. Shops and restaurants will offer special promotions, refreshments, and pop-up events throughout the day.
Holiday Events in Montgomery County
Winter City Lights
Dates: November 28 to December 29
Location: Olney, Maryland
Winter City Lights is one of the largest light displays in the Mid-Atlantic, featuring towering illuminated structures, a 52-foot Christmas tree, and a canopy of lights choreographed to your favorite holiday songs. Don’t miss the eight-lane Penguin Plunge snow tubing ride, cozy fire pits, and holiday treats.
Winter Lights Festival
Dates: November 28 to December 31 (Closed December 25)
Location: Seneca Creek State Park, Gaithersburg
Now in its 30th year, this 3.5-mile drive-through display features more than 450 light installations and beautifully lit trees. It’s a magical family tradition that celebrates the season in a serene natural setting.
Bethesda Winter Wonderland & Holiday Market
Date: December 6
Location: Norfolk & Cordell Avenues, Downtown Bethesda
Celebrate the season with Santa visits, live ice sculpting, face painting, and performances from local schools and community groups. Be sure to visit the URBN Holiday Market featuring 50 artisans and bring a new toy to donate to Toys for Tots.
Experience the Magic of the Holidays Close to Home
Whether you’re catching a game at the Military Bowl, shopping at Midnight Madness, or driving through Lights on the Bay, the Annapolis region is brimming with holiday cheer. From downtown charm to dazzling light displays, there’s no shortage of ways to celebrate the season right here at home.
If you’re considering making Annapolis or Anne Arundel County your home for the holidays and beyond, our team at Bay to Beltway can help you find the perfect place to call home.
Contact us today to learn more about living in one of the most festive and welcoming communities in Maryland.
