Oxford Christmas Events & Things to Do 2025

Experience the heartwarming tradition of Christmas in St. Michaels, celebrating 39 years of community service. This beloved event offers a chance to create lasting holiday memories while supporting local non-profit organizations. Purchase the exclusive 2025 Limited Edition Collectors Ornament, with all proceeds directly benefiting the Bay Hundred community. Join in...

Get ready for Midnight Madness, a special late-night shopping event in St. Michaels. Local businesses open their doors for extended hours, offering a festive atmosphere for holiday shoppers. It's the perfect opportunity to find unique gifts and enjoy the start of the holiday season in a charming setting.

Discover a showcase of local talent at the Annual Craft and Home Vendor Show. This event brings together a variety of crafters and vendors offering unique handmade goods and home decor items. It's the perfect place to find distinctive gifts and decorative pieces.

Step into a festive Downtown Annapolis Winter Wonderland during Midnight Madness. This cherished holiday tradition invites you to stroll through streets adorned with twinkling lights, festive decorations, and a towering Christmas tree. Enjoy extended shopping hours until midnight, discover unique gifts from local boutiques, and soak in the magical atmosphere...

Experience a unique holiday spectacle as decorated boats illuminate the waterways in a dazzling parade. This event offers a festive maritime twist on traditional light displays, showcasing creative and vibrant holiday decorations on vessels.

Experience the magic of Lights on the Bay, a cherished annual drive-through holiday light show at Sandy Point State Park. This two-mile scenic journey along the Chesapeake Bay features over 70 dazzling animated and stationary light displays, including a special Santa's North Pole train station. The event supports the SPCA...

Experience the magic of the holiday season at the Solomons Christmas Walk and Tree Lighting. This beloved annual event transforms Solomons Island into a festive wonderland. Visitors can enjoy live musical performances, meet Santa Claus, and delight in the cheerful presence of the Otter mascot. The Museum Store offers a...

Ring in the New Year with an unforgettable celebration on the water in Annapolis. This exclusive yacht party offers a DJ, dancing, and a complimentary beverage, all while providing a front-row seat to the city's 9:00 PM fireworks display. Alcoholic and non-alcoholic drinks are available for purchase from the full-service...

Get ready for a decadent celebration of all things chocolate at the Annapolis Chocolate Binge Festival! This family-friendly event transforms the first block of West Street into a chocolate lover's paradise. Alongside a delightful array of chocolate vendors, the festival hosts an exciting Gingerbread House decorating contest, inviting everyone from...

Ballet Theatre of Maryland presents a captivating, Annapolitan-inspired Nutcracker. This unique production reimagines the beloved classic with local historical elements, vibrant costumes, and original choreography. Follow Clara's dream journey through 19th-century Annapolis, from snow-dusted gardens to a Land of the Sweets filled with local confections. It's a festive holiday treat...

Get ready for a spectacular holiday celebration at the Talbot Street Parade! This beloved event features a dazzling procession of marching bands, antique vehicles, fire engines, horses, and unique acts like kazoo bands and llamas. The grand finale includes the arrival of Santa and Mrs. Claus, marking a joyous start...

Lace up your running shoes for the Santa Fun Run 5k for Hospice, a festive 5k run/walk that supports Talbot Hospice. Participants are encouraged to wear holiday costumes and festive attire as they race through Easton. The event also offers a virtual option for those who wish to participate remotely....

Get ready for a magical evening at 'A Budweiser Clydesdale Miracle on West Street,' a festive prelude to the Military Bowl. This event features the renowned Budweiser Clydesdales, alongside a vibrant street scene with food trucks, vendors, and engaging activities for all ages. It's the perfect way to kick off...