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 are the many stores, restaurants, and businesses that support the Downtown Annapolis Partnerships efforts to put on events like Midnight Madness in downtown Annapolis. Please be sure to visit them.

Annapolis Shopping / Retail / Gallery

Alpaca International - alpaca clothing boutique

Blanca Flor Silver Jewelry - sterling silver jewelry boutique

Capital Comics - comic book store

The Gateway Florist - flower and gift shop

Graul's Market - grocery store

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

Hobo - handbag boutique

Irish Traditions - Irish clothing and gift boutique

Lilac Bijoux - clothing boutique

Local by Design - local artisans shop

The Lucky Knot - clothing boutique

Maryland Federation of Art - gallery

Mills Fine Wine & Spirits - wine shop

Museum Store - gift shop

Shades of The Bay - sunglass and flip flop specialty store

Sheehy Lexus - car dealership

The Spice & Tea Exchange - seasoning and tea shop


Annapolis Restaurants & Food

Annapolis Market House - Annapolis cuisine

Blackwall Hitch - coastal cuisine

Buddy's Crabs & Ribs - seafood and ribs

Caliente Grill - Latino cuisine

Carpaccio Tuscan Kitchen - Italian cuisine

Chart House - seafood restaurant

Chick and Ruth's Delly - deli and bakery

Federal House Bar & Grille - bar and grille

Galway Bay Irish Restaurant - Irish pub

Iron Rooster - southern cuisine specializing in breakfast 

Kilwins - ice cream and chocolate shop

Latitude 38 Waterfront Annapolis - seafood restaurant including Club 38 wine club

Level - a small plates lounge

Light House Bistro - social enterprise restaurant

Mason's Famous Lobster Rolls - lobster roll restaurant

McGarvey's Saloon and Oyster Bar - seafood and oyster bar

Middleton Tavern - Chesapeake cuisine

Miss Shirley's Cafe - Southern-inspired breakfast, brunch, and lunch

Mission BBQ - barbeque restaurant

O'Brien's Oyster Bar - seafood restaurant and bar

Paul's Homewood Cafe - Greek and American cuisine

Rams Head Tavern - American tavern fare

Rasa Juice Shop - juice shop

Reynolds Tavern - teahouse and pub

Stan and Joe's Saloon - American pub fare


Annapolis Hotel / Inns

Flag House Inn - bed & breakfast

Georgian House - bed & breakfast

Hilton Garden Inn Annapolis Downtown - hotel, conference rooms and restaurant

The Hotel Annapolis - hotel, conference rooms, ballroom and restaurant


Annapolis Events

Turning Point Sports - sports and teambuilding events


Annapolis Press / Publications / Radio

Eye on Annapolis  - online publishing/news

N2 Publishing - publishes Life on the Hill magazine

SpinSheet Publishing Company - Chesapeake Bay Sailing Magazine

What's Up Magazine - events magazine

WNAV - radio


Annapolis Performing Arts / Entertainment / Museums

Annapolis Summer Garden Theatre - Outdoor theatre

Annapolis Symphony Orchestra - performing arts organization

Maryland Hall - performing and visual arts and education center

Mission Escape Rooms - interactive escape room experience

Mitchell Gallery - art gallery within St. John's College


Annapolis Tours / Visitor Services / Tourist Attractions

Hammond-Harwood House - historic mansion and museum with tours

Historic Annapolis Foundation - historic sites including Hogshead and William Paca House 

Schooner Woodwind - Annapolis sailing cruises

Urban Eventours - transportation services and tours

Visit Annapolis - visitors center

Watermark - boat tours and charters


Annapolis Services and Groups

Annapolis Jaycees - community service 

Campbell Property Management LLP - property management

Chesapeake Property Management Realty, LLC - property management

The City of Annapolis - local government

Fleet Reserve Club of Annapolis - Veterans organization

Gohn Hankey & Berlage LLP - law firm

Herrmann Advertising - marketing and branding firm

Naval Academy Business Service Division -  Naval Academy Visitors Center and gift shop

St. John's College - liberal arts college

W&P Nautical - nautical property management and boat slips






"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: