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Maryland 2025 Winter Holiday Events

3 days ago

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Snowflake ornaments with winged star emblems hang on a snowy branch. One is blue with stars, the other maroon. Festive and bright.

As we embrace the winter season, the Maryland Veterans Chamber of Commerce is proud to highlight the many opportunities available for veterans, military veterans, and their families across Maryland. December 2025 brings a wealth of events where veteran-owned businesses can participate, network, and help stimulate the local economy while celebrating the spirit of veterans supporting veterans.


Holiday Markets and Vendor Opportunities

One of the best ways for veteran-owned businesses to boost visibility and sales during the holiday season is by participating in Maryland's renowned holiday markets. These events draw thousands of shoppers looking for unique, locally made gifts. It’s perfect for showcasing veteran-owned products and services.


Baltimore Christmas Village at Inner Harbor

Running from November 22 through December 24, 2025, the Baltimore Christmas Village transforms the Inner Harbor's West Shore Park into an authentic German Christmas market experience. With over 50 vendor booths featuring handcrafted goods, this event presents an excellent opportunity for veteran-owned businesses in the artisan and specialty food sectors. The market operates Sunday through Thursday from 12pm to 8pm, and Friday through Saturday from 12pm to 9pm.


Kris Kringle Christmas Market – Charles County

December 12-14, 2025 at the Charles County Fairgrounds, this beloved community event features over 180 local artisans and crafters. The market includes live music, a Christmas tree lighting, fireworks, and children's activities. With a modest $5 admission fee benefiting local organizations including the Southern Maryland Food Bank and Charles County Volunteer Fire and EMS, this event exemplifies the spirit of veterans supporting veterans and community service that defines our chamber of commerce values.


Additional December Markets

•  Annapolis Christmas Market (December 4-7) – Four days of artisan shopping at 1 Dock Street, including the popular Midnight Madness shopping event and Eastport Light Parade

•  Spirit of Calvert Christmas Market (December 6-7) – Two-day event at Calvert County Fairgrounds with vendors, festive displays, and family activities

•  Annmarie Holiday Market (December 6 & 13) – Seasonal outdoor market at Annmarie Sculpture Garden featuring handmade goods

•  College Park Winter Wonderland (December 6) – Annual holiday market and tree lighting at City Hall Plaza from 2pm to 8pm

•  Downtown Hagerstown Holiday Market (December 22nd) – University Plaza hosts live music, Santa visits, and holiday crafts

Networking and Business Development Events

Beyond traditional holiday markets, December offers opportunities for veteran-owned businesses to strengthen their networks and develop new partnerships.


Baltimore Peninsula Holiday Programming

Throughout December, the Baltimore Peninsula district hosts holiday programming including maker's markets, waterfront fitness classes, and community events. The annual tree lighting at Sagamore Spirit on December 5 features distillery tours, live music, and local food vendors—an excellent networking opportunity for veteran entrepreneurs in the food, beverage, and hospitality industries.


Chamber of Commerce Resources

The Maryland Veterans Chamber of Commerce continues to connect veteran-owned businesses with resources year-round. Our members gain access to networking events, government contracting opportunities, and business development workshops. The SBA's Veterans Business Outreach Centers (VBOCs) offer no-cost counseling, business plan development, and training specifically designed for the military veteran entrepreneur.


Key programs to explore include the Boots to Business program for transitioning service members, SCORE mentorship connecting veteran entrepreneurs with experienced business professionals, and the Service-Disabled Veteran-Owned Small Business (SDVOSB) certification for federal contracting opportunities.


Supportive Services for Veteran Families

The holiday season can be challenging for some veteran families, and Maryland offers robust supportive services for veteran families through various programs and organizations.


SSVF Program Resources

The Supportive Services for Veteran Families (SSVF) program provides crucial assistance to very low-income veteran families who are homeless or at risk of homelessness. In Maryland, SSVF grantees provide case management, housing counseling, and temporary financial assistance. Veterans in Baltimore City and County can contact 410-576-9626 for assessment and services.

Community Events and Family Activities

December in Maryland offers wonderful opportunities for veterans and their families to celebrate the season together.


Miracle on 34th Street – Hampden, Baltimore

This nationally recognized holiday light display in Baltimore's Hampden neighborhood runs from the Saturday after Thanksgiving through New Year's Eve. The tradition, started by a local couple over 70 years ago, features spectacular decorations including the famous hubcap tree and bicycle wheel snowman. It's a free, family-friendly attraction that showcases the best of Baltimore community spirit.

Sandy Point State Park Lights on the Bay

Drive along the scenic Chesapeake Bay shore to experience over 70 animated light displays along a stunning two-mile route. This holiday tradition offers a magical experience for veteran families seeking affordable, memorable activities during the season.

Downtown Annapolis Holiday Celebrations

Maryland's historic capital city offers festive experiences including Snowflake Alley's twinkling lights, the Chocolate Festival on West Street, and free holiday parking downtown between Thanksgiving and New Year's Day. The Eastport Yacht Club's Light Parade brings nautical holiday spirit to the waterfront.


How Veteran-Owned Businesses Can Participate

If you're a veteran entrepreneur looking to maximize December opportunities, consider these action steps:


•  Register Early for Markets: Many holiday markets have limited vendor space. Contact event organizers now to secure your spot for remaining 2025 dates or to get on the list for 2026.

•  Get Certified: Consider obtaining SDVOSB certification through the SBA or certification through the National Veteran Business Development Council (NVBDC) to access corporate and government contracting opportunities.

•  Join a Chamber of Commerce: Membership in the Maryland Veterans Chamber of Commerce connects you with fellow veteran business owners, resources, and exclusive networking events.

•   Partner with Other Veterans: Consider collaborative booths or cross-promotions with other veteran-owned businesses to maximize visibility and share costs.

•    Give Back: Participate in events that support veteran causes—it builds goodwill, strengthens your network, and embodies the spirit of veterans supporting veterans.


Supporting Maryland's Veteran Economy

Every purchase from a veteran-owned business directly supports the military veteran community and strengthens Maryland's economy. According to the SBA, veteran-owned businesses account for approximately 9% of all U.S. companies, employing millions of Americans and generating billions in payroll annually. When consumers choose to shop at veteran-owned businesses this holiday season, they're investing in entrepreneurs who bring unmatched discipline, resourcefulness, and dedication to the marketplace.


The Maryland Veterans Chamber of Commerce encourages all Marylanders to seek out and support veteran-owned businesses this December. Whether you're shopping at a holiday market, hiring a veteran-owned service provider, or connecting veteran entrepreneurs with opportunities, you're contributing to a vibrant ecosystem of veterans supporting veterans.


For more information about joining the Maryland Veterans Chamber of Commerce, finding veteran affairs resources, or learning about supportive services for veteran families, visit our website or contact us directly. Together, we can make this holiday season successful for veteran-owned businesses across Maryland.

3 days ago

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