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Midnight Madness
Annapolis, MD
Historic streets transformed into a winter wonderland with live entertainment.
About
Experience the enchantment of Midnight Madness, a cherished holiday tradition in Historic Downtown Annapolis. Streets and storefronts shimmer with festive decorations, transforming the area into a dazzling winter wonderland. Stroll along Main Street, West Street, and Maryland Avenue, where shops offer special refreshments and sales, making it the perfect opportunity for holiday shopping and discovering why Annapolis is a top Christmas town.
Our Take
Family Friendly
Best For
Holiday shopping and festive atmosphere
Vibe
Festive, charming, community-oriented
Energy Level
Moderate
Budget
Variable (Free To Attend, Shopping Costs Vary)
Photo Friendly
High
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.
Location
Event Details
Duration
4 pm - Midnight/11 pm
Ages
All ages
Schedule
The first two Thursdays of December from 4 pm until Midnight and the third Thursday of December from 4 pm until 11 pm
Featured Performers
- carolers
- choirs
- musicians
- other street performers
Organizer
Downtown Annapolis Partnership
Practical Information
Parking
Free parking at Calvert Street Parking Garage (6 pm-6 am), free short-term 2-hour parking on commercial streets, free 2-hour parking for city residents at Hillman Garage, $2 parking at Whitmore Parking Garage (4 pm-6 am). Free circulator buses and shuttles available.
Pet Policy
Service animals welcome
Food & Drink
Shops will have refreshments and sales; merchants may offer complimentary refreshments.
Quick Actions
Tips & Advice
- Arrive early on the first two Thursdays of December to fully experience the extended hours until midnight and take advantage of the widest selection of shopping and entertainment.
- Utilize the free circulator buses and shuttles to easily navigate between parking garages and various shopping districts, especially if you plan to visit multiple areas.
- Check the Downtown Annapolis Partnership website for specific merchant specials and refreshment offerings announced closer to the event dates to maximize your shopping experience.
- Wear comfortable shoes suitable for walking on historic brick-lined streets and be prepared for potential crowds, especially during peak evening hours.
- Don't miss the unique photo opportunities, including the Holiday Light Canopy and Snowflake Alley, to capture memories of this festive Annapolis tradition.
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 of December from 4 pm until 11 pm. It's always best to confirm the exact dates for the current year.
Is there parking available, and is it free?
Yes, there are several parking options. Free parking is available at Calvert Street Parking Garage from 6 pm to 6 am. Short-term 2-hour parking is free on commercial streets. City residents can get 2 hours of free parking at Hillman Garage. Additionally, Whitmore Parking Garage offers $2 parking from 4 pm to 6 am. Free circulator buses and shuttles are also provided.
What kind of entertainment can I expect?
The streets will be alive with free on-the-street entertainment, including carolers, choirs, musicians, and other street performers, creating a vibrant holiday atmosphere.
Are there opportunities for holiday shopping?
Absolutely! Midnight Madness is an ideal event for holiday shopping, with numerous shops, galleries, and boutiques offering refreshments, sales, and unique gift ideas. The Annapolis Holiday Market is also available during the second event.
Can I bring my pet?
While the event is generally geared towards families and shoppers, the specific pet policy is not detailed. However, service animals are typically welcome at such events.