Midnight Madness
2026 dates not announced yet. Details are from 2025.
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 with live entertainment and carolers.
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Plan Your Visit
Website / Tickets
Tickets
$
Ages
All ages
Neighborhood
Downtown Annapolis
Featured Performers
- Carolers
- Choirs
- Musicians
- Street performers
Food & Drink
Participating shops and restaurants will have refreshments and sales. Complimentary refreshments may be offered by downtown merchants.
Parking
Free parking available at Calvert Street Parking Garage (6 pm-6 am). Short-term 2-hour free parking on commercial streets. City residents get 2 hours free at Hillman Garage. $2 parking at Whitmore Parking Garage (4 pm-6 am). Free circulator buses and shuttles available.
Going?
Location
Tips & Advice
- Arrive early on the first two Thursdays to maximize your shopping time before midnight, and check the Annapolis Parking website for the most up-to-date shuttle routes.
- Consider visiting the Annapolis Holiday Market on the City Dock during the second Midnight Madness event for additional festive finds.
- Dress warmly and wear comfortable shoes, as you'll be strolling through historic streets, and many shops will offer complimentary refreshments.
- Take advantage of the various parking options, including free garage parking and short-term street parking, to make your visit convenient.
- Look for special offers and personalized service from local merchants, which are hallmarks of this community-focused shopping event.
Special Events & Promotions
- Extended shopping hours until midnight
- Participating shops and restaurants offer refreshments and sales
- Annapolis Holiday Market on the City Dock (during second Midnight Madness)
Links & Contact
Christmas Events Near Me is an independent guide, not the organizer of this event. For tickets, entries, vendor spots or questions, contact the organizer directly through their contact page.
Frequently Asked Questions
What are the specific dates and times for Midnight Madness?
The event typically takes place on the first two Thursdays of December from 4 PM until Midnight, and the third Thursday from 4 PM until 11 PM. It's best to confirm the exact dates for the current year.
Where can I find parking during Midnight Madness?
Several parking options are available, including free parking at Calvert Street and Hillman Garages (with time limits), paid parking at Whitmore Garage, and free short-term street parking. Free shuttles are also provided.
What kind of entertainment can I expect?
Attendees can enjoy a festive atmosphere with carolers, choirs, musicians, and other street performers throughout the downtown area.
Are there opportunities for holiday photos?
Yes, the event offers fun photo opportunities for all ages amidst the festive decorations, including the Holiday Light Canopy and Snowflake Alley.
Can I shop online if I can't attend in person?
Yes, many downtown Annapolis stores offer online shopping options, and you can also purchase local restaurant gift cards online.
Browse Christmas in Annapolis
Always check the official website for the most current information.
We've done our best to keep details up-to-date, but event schedules, prices, and policies can change. For the latest updates, please visit the official website or contact the organizers directly. Christmas Events Near Me is an independent guide and isn't affiliated with the events we list.