Annapolis Arts District

Annapolis Arts DistrictWhen the sun goes down the holiday lights turn on in downtown Annapolis, creating a festive destination for a family outing. Special shopping hours and activities during Midnight Madness and Eleventh Hour add to the seasonal fun along Main Street, West Street, Maryland Avenue, State Circle and Dock Street.

A new lighted canopy stretches across West Street in the arts district, and lights and greenery wrap the poles of downtown.

Don’t miss Snowflake Alley with bright snowflakes lighting the way in the narrow alley between Main Street and the shops and restaurants on State Circle and Maryland Avenue.

Snowflake Alley in AnnapolisChoirs, choruses and bands add a musical backdrop during Midnight Madness II, Dec. 10, when stores are open until midnight, and Eleventh Hour, Dec. 17, with stores open until 11 p.m.

On Dec. 10, kids — and adults — can pet a baby alpaca and enjoy cookies and spiced tea at Alpaca International on Main Street 6-11 p.m. Enjoy the Festival of Lights when the menorah at Susan Campbell Park at City Dock lights up in the early evening with help from Chabad of Anne Arundel County and Mayor Mike Pantelides, followed by the traditional service and songs.

Cousin Eddie plays at the Christmas Tree 8:30-11 p.m. and Jeremy Ragsdale’s The Lead Singer Holiday Edition Concert is 6:30 p.m. at O’Brien’s Oyster Bar and Restaurant.

During Eleventh Hour on Dec. 17, shoppers can relax and stretch with special yoga stretching for shopping at West Street Park.

Other musical performances include:

  • Christmas Tree: Bay Area Community Church 6-8:30 p.m. (Dec. 10 and 17)
  • Bell Ringer: Salvation Army Band (Dec. 10 and 17)
  • Pocket Park: St. Anne’s Middle School Chorus (Dec. 10); Fast as Lightning (Dec. 17)
  • Outside MSTA Building: All Children’s Chorus of Annapolis (Dec. 10); Temple Beth Shalom Child’s Chorus (Dec. 17)
  • Porch at Maryland Inn: Bates Middle School Performing Arts Choir (Dec. 10)
  • West Street Park: Arundelair Chorus (Dec. 10); Yoga Stretching for Shopping (Dec. 17)
  • Outside Red Red Wine and Castle Bay: Freedom Chorus (Dec. 10)
  • Paws Pet Boutique: Joliana from Chasing Levity (Dec. 10 and 17)
  • Snyder’s Bootery: Green Line Brass Quintet (Dec. 10 and 17)
  • Strolling: Sons of Severn Chorus and Chesapeake Revelers (Dec. 10 and 17) and Voices of Pride (Dec. 17)

Star Wars in the window at Annapolis Ice Cream CompanyWarm up with hot chocolate from a coffee shop or stop in one of the many ice cream destinations for a treat. Check out Darth Vader in the window of The Annapolis Ice Cream Company.

Take advantage of the extended free holiday parking and three-hour free valet service for easier parking. The valet service is at Market Space and is available Thursday-Sunday until Dec. 24. The Circulator Trolley will be free during Midnight Madness and Eleventh Hour, moving visitors from the parking garages Hillman, Gott’s, Knighton and Park Place around downtown.

Find more information about Midnight Madness and Eleventh Hour in Annapolis at the Annapolis Partnership website

Find more fun things to do during the holidays in our Holiday Countdown.