Midnight Madness

Snow Flake Alley is on Google Maps!  Take a virtual stroll down the alley here - but make sure you visit in person, too!

Parking tips for downtown Annapolis

Our free circulator bus that runs throughout downtown Annapolis.

The historic downtown Annapolis area is a beautiful small area that is easily walkable or bikeable from any of our parking garages or parking lots.  The majority of on-street parking is limited to 2-hour parking, this is perfect for those coming in for a short time and need quick access to their favorite store or restaurant. For those coming to spend longer periods of time, the parking garages all allow for all-day parking at very reasonable rates.  All of the downtown parking garages are also served by a free circulator shuttle that runs every 20 minutes throughout downtown Annapolis. There are designated stops and you can also waive to the driver and they will stop and pick you up. See the circulator shuttle's current location and route by clicking here.

Special Parking Deals for the Holidays between Thanksgiving and Christmas in addition to our favorite tips listed below.
Free Parking for Small Business Saturday (Nov 30) and Midnight Madness events (December 5, 12 and 19) at Whitmore Parking Garage (25 Clay Street)
3 Hour free parking EVERY DAY at all on-street metered spaces when you enter the promo code ParkDTA into the Park Mobile App
Small Business Saturday, November 30 - $5 all-day parking at Gotts Court and Knighton Parking Garages when you prepay at www.annapolisparking.com
Thursdays December 5, 12 and 19 - $5 all-day parking at Gotts Court and Knighton Parking Garages when you prepay at www.annapolisparking.com
Below are our favorite parking tips for downtown Annapolis that you can use all year!
Free Parking  Garage Options
1) State Parking Garage (19 St. Johns Street) Free weekdays starting at 6 pm and free all day Saturday and Sunday
2) Whitmore Parking Garage (25 Clay Street) is free on Sundays until 4 pm or $2 all-day Sundays. 
3) Hillman, Gotts, Knighton and Park Place Parking Garages are free on Sundays until 1 pm.
Free parking for City of Annapolis Residents for 2 hours at Hillman, Gotts, Knighton and Park Place Parking Garages. Visit Annapolis Parking at 60 West Street and Park Place Parking Garage to get your free parking passes.
Earn free parking with Park and Shop. Make a purchase from select retailers and restaurants and they will give you vouchers for free parking in city-owned parking garages including Hillman, Gotts Court, Knighton and Park Place parking garages. Click here to learn more about participating locations and details. Businesses can sign up for this program at 60 West Street. 
$2 Parking for all evenings at Whitmore Parking Garage (25 Clay Street) starting at 4 pm every day.
$5 evening parking after 8 pm at Gott's Court Parking Garage
New Parking lot - The school board parking lot next to Annapolis Summer Garden Theatre is now open to the public in the evenings and weekends.
Parking garages are cheaper the farther you park from City Dock i.e. Park Place, West Garrett, Knighton, Whitmore and Gotts Parking Garages. They all offer a free circulator shuttle that runs along West Street, Calvert Street, State Circle, Duke of Gloucester and Main Street every 20 minutes.
Employee Parking starts at just $2 all day if you park at  Park Place Parking Garage plus get a free shuttle to downtown. Gotts and Knighton Parking Garages offer discounted $2 employee evening parking starting at 3 pm. Hillman Parking Garage has discounted evening employee parking for $5 after 3 pm. Employers can sign up for their employees at 60 West Street.
Free Circulator Bus now stops at every downtown Annapolis Parking Garage and takes you to West Street, Calvert Street, St John College, State House, Duke of Gloucester Street, City Dock and Main Street.
Bike Share and bike parking
New Pace Bike Share has arrived. Current locations include the Market House, behind Chick and Ruth's Delly, Whitmore Park, Banneker-Douglas Museum and the Graduate Hotel(formerly the Loews Hotel). Download the Pace Bike Share App to see all the bike share locations and to rent a bike today.  If you are riding your own bike into town click here for all bike rack locations to park your bike. This is a great way to travel into town for those living or staying nearby. Plus you get a little exercise and save the planet at the same time.
Arrive by bus, taxi or other popular rideshare programs and you can avoid having to drive or park. 
For more parking information including addresses of all parking garages and parking rates go to www.annapolisparking.com


Midnight Madness – A Festive Shopping Celebration in Downtown Annapolis 2019

Thursdays, December 5 and 12 from 6PM until Midnight and December 19 from 6PM until 11PM

Experience Midnight Madness in Annapolis

Downtown Annapolis Partnership proudly presents Midnight Madness—a Historic Downtown Annapolis holiday tradition that encompasses the charm and character of our most beloved memories of Norman Rockwell and Charles Dickens. We will adorn the streets and participating storefronts with holiday decorations, trees, garland, snowflakes, bows and lights to create a Downtown Winter Wonderland. Residents and visitors are invited to stroll along Main Street, West Street, Maryland Avenue, State Circle, and Dock Street from 6 PM until Midnight to support our local businesses. When we Shop Local, we reinvest in our community and help our downtown businesses thrive. Check out all the stores, galleries, and boutiques along West Street, Maryland Ave, State Circle, Main Street, Market Space, Randall Street, and Dock Street.

A very special thank you to our premier sponsor, Sheehy Lexus of Annapolis for their ongoing support!

Some of our Featured Attractions:

  • Holiday Light Canopy over West Street / Annapolis Arts District
  • Snowflake Alley: A magical passageway to a delightful evening of fun, entertainment, shopping deals and treats to eat. | Main Street (Cabbage Alley)
  • Holiday Christmas Tree at Market Space

Our historic, brick-lined streets will be full of carolers, choirs, musicians, and other street performers. We will offer fun photo opportunities for all ages. Downtown merchants may offer complimentary refreshments, specials, shopping incentives and a personalized approach to customer service that is certain to create a delightful sense of community and belonging. Please join us!

To make your experience more enjoyable:

  • The Calvert Street Parking Garage is Free Parking between 6 pm and 6 am. Located  at 19 St Johns Street
  • Use the Park & Shop program is earn free parking at Hillman, Gott's Court, Park Place and Knighton Parking Garages.
  • The Whitmore Parking Garage is free from 4 pm to 6 am. Located at 25 Clay Street.
  • $5 parking at Park Place and Knighton Parking Garages when you prepay at www.annapolisparking.com 
  • Free Circulator buses run along West Street, Calvert Street, State Circle, and Main Street.


Midnight Madness – Annapolis 2019

Here is just some of the many stores you will find at Midnight Madness in downtown Annapolis


Annapolis Shopping / Retail / Gallery

Alpaca International - clothing boutique

Annapolis Arts Alliance Popup Store - gift, art, and craft gallery

The Annapolis Pottery - pottery store and studio

Back Creek Books - specialty book shop

Blanca Flor Silver Jewelry - sterling silver jewelry and gifts

Capital Comics - comic book store

Graul's Market - grocery store

HERE. a pop-up shop - pop up gift boutique

Hobo International - Handbag Boutique 

Irish Traditions - Irish clothing and gift boutique

Lilac Bijoux - clothing boutique

The Lucky Knot - clothing boutique

Maria's Picture Place & Gift Shop - gallery, picture framing & gift shop

Maryland Federation of Art - gallery

The Pink Crab - clothing boutique

Mission Escape Rooms - interactive escape room experience

RASA juice shop - vegan, gluten-free food and juice shop

Sheehy Lexus - car dealership

The Spice & Tea Exchange - seasoning and tea shop

TTR Sotheby's International Realty - real estate services

Tyler Bo - clothing boutique

Woodcraft Artisans - home decor

Zachary's Jewelers - fine and custom jewelry


Entertainment & Tours

Cruises on the Bay - Watermark - Take a ride on the Jolly Express

Mission Escape Rooms - interactive escape room experience

Urban Eventours - transportation services and tours


Annapolis Restaurants & Food

Buddy's Crabs & Ribs - seafood and ribs

Caliente Grill - Latino cuisine

Carpaccio Tuscan Kitchen - Italian cuisine

Chick and Ruth's Delly - deli and bakery

Federal House Bar & Grille - bar and grille

Galway Bay Irish Restaurant - Irish pub

Kilwins - ice cream and chocolate shop

Level A Small Plates Lounge - cocktails and tapas style cuisine

Light House Bistro - social enterprise restaurant

Middleton Tavern - Chesapeake cuisine

Miss Shirley's Cafe - Southern style breakfast and lunch

Mission BBQ - barbeque restaurant

O'brien's Steakhouse - Chesapeake cuisine

Rams Head Tavern - American tavern fare

Reynolds Tavern - teahouse and pub

Stan and Joe's Saloon - American pub fare

Starbucks - coffeehouse


Annapolis Hotel / Inns

Annapolis Waterfront Hotel - hotel and conference/ballrooms

Georgian House - bed & breakfast

Historic Inns of Annapolis -  historic inns and conference rooms




"CoCo with the PoPo"

Annapolis - A National Treasure

There is no prettier time of the year to visit our beautiful City of Annapolis. We were voted one of America's Best Towns for The Holidays by Travel and Leisure. Make plans to enjoy your holiday season in Annapolis

Snowflake Alley


Make your holidays brighter with these specials from our local businesses: