If you’re looking for a little holiday magic this season, look no further than these festive Chesapeake Bay towns. Before heading out to any of the below events, be sure to double-check the event websites directly, as things change rapidly in 2020!

holiday magic
Get in the holiday spirit during these events around the Chesapeake. Pictured is Midnight Madness in Annapolis. Photo courtesy of the Downtown Annapolis Partnership

Lights on the Bay at Sandy Point State Park

November 23 to January 1 from 5 – 10 p.m. nightly, weather permitting. 

Don’t miss this spectacular drive-through holiday lights show beside the Chesapeake Bay. The event features more than 60 animated and stationary displays, including traditional Maryland-themed favorites, holiday, and children’s displays. Proceeds benefit the SPCA of Anne Arundel County. Admission: $15, car; $50, bus. 

holiday magic
From the Swashbuckling Undersea Adventure at Lights by the Bay 2019. Photo courtesy of facebook.com/lightsonthebayMD

Midnight Madness in Annapolis

December 5 and 12 (6 p.m. to midnight) and December 19 (6 to 11 p.m.)

Historic Annapolis shops throw open their doors in a glorified block party that is open to all. Enjoy musical performances as well as food and refreshments at many stores as you stroll along Main Street, State Circle and Maryland Avenue, and the Arts District in search of that perfect gift. 

Festivities in Yorktown, VA:

  • Christmas Tree Lighting, December 4 at 7:30 p.m. at Riverwalk Landing
  • Christmas Market on Main, December 5 (10 a.m. to 3 p.m.) and December 6 (11 a.m. to 3 p.m.) on Historic Main Street. Whether you’re searching for a holiday gift for family and friends or as a treat to yourself, you’re sure to find it at one of the most anticipated Historic Yorktown events. Close to 60 vendors will line the street in a socially distanced set-up, selling everything from local art, such as paintings, jewelry, and photography, to breads, sweets, and other goodies. Get your greenery and Christmas wreaths, too. 

Festive Fridays in Cape Charles, VA

December 4, 11, and 18 from 5 to 8 p.m.

Shop, savor, stroll, and stay in the coastal Chesapeake Bay beach town of Cape Charles. Celebrate with carriage rides, street performers, live local music, restaurant specials, food trucks, B&Bs, Santa and Mrs. Claus, and kids’ activities. Free. 

Mount Harmon Open Air Yuletide Festival and Holiday Marketplace

December 5-6, 11 a.m. to 3 p.m.

This festive event, re-imagined for pandemic times, features Mount Harmon’s open-air yuletide decorations and greens sale, artisan marketplace and museum gift shops, hearth cooking, and self-guided yuletide walking tours of the mansion’s beautifully decorated historic buildings and grounds. Tickets: $10, Friends of Mount Harmon members $5. 

Old Fashioned Christmas in Elkton, MD

December 18 from 5-8 p.m.  

A pandemic-friendly version of an Old Fashioned Christmas will unfold in the town of Elkton. Find updates on the website.

Virtual Christmas in St. Michaels

Celebrate a virtual Christmas in St. Michaels. Buy tickets for the November 15 raffle to win a helicopter tour and lunch for four. Preview the Online Auction beginning November 20 and bid on fabulous items. Shop online for unique gifts and holiday treats. Enjoy the “Light up the Night” Drive-by House and Harbor Tour, and more. For details visit christmasinstmichaels.org or follow on Facebook and Instagram.