Annapolis Christmas Lights Trail: A Holiday Walking Guide Through Historic Downtown

Stunning Downtown Annapolis Holiday Lights

Few locations can match the beauty and charm of downtown Annapolis during the holiday season. At night, this town is truly magical! Its 18th-century colonial architecture, cobblestone sidewalks, and picturesque waterfront are all beautifully lit with colorful holiday lights. That's why I've created this easy-to-follow Annapolis Christmas Lights Trail. Below are some highlights of this festive holiday walking adventure.

Annapolis Christmas Lights Walking Route (With Detailed Map)

Map for Annapolis Holiday Lights Walking Tour

I've mapped out the perfect 1.5-mile loop to view the best holiday lights in downtown Annapolis, MD. It's a must-do to round out your holiday season!

Here is a link to Plotaroute for your gps guided tour.

1. Hillman Parking Garage

   The walking tour will start at the entrance of the Hillman Parking Garage in downtown Annapolis. I recommend parking here as it's super convenient, and the first hour is free during the holday season. The garage is located at 150 Gorman Street, Annapolis.

   
   

2. Randall Street & Annapolis City Dock

   Continuing down Main Street towards the waterfront, you'll arrive at Randall Street. This is where the main Christmas Tree and Santa's Reindeer are located. All of the shops and stores are decked out with holiday cheer.

   Next, you'll head to the Annapolis City Dock area. It's always fun to stroll near the water and see the boats docked in Ego Alley. On the opposite side, The Choptank Restaurant has done a fantastic job decorating for the holidays.

   
   
   

   Randall Street Holiday Lights

   

   Annapolis Downtown Christmas Tree

   

   The Choptank Restaurant Holiday Decor

3. Maryland Avenue

   After visiting the Annapolis City Dock, this walking tour leads you up Prince George Street toward Maryland Ave. As you go, you'll pass through a charming neighborhood with houses delightfully adorned for the season.

   You'll know when you've reached Maryland Ave by the charming snowflake lights strung across the street. This quaint area is one of Maryand's most historic streets, filled with delicious restaurants, unique shopping and fascinating art galleries.
   

   

   Maryland Ave Holiday Lights

4. Maryland State Circle & Governor's Mansion

   The walk continues around State Circle, with The Maryland State House located at its center. Although this building wasn't decorated for the holidays, it still was beautiful none-the-less.

   Make sure to look to your right as you progress around the circle to see the Governor's Mansion. Built in 1870, this stately home is elegantly illuminated and decorated for Christmastime.
   

   

   Maryland Governor's Mansion During Christmastime

5. Church Circle & West Street

   Church Circle is easily the heart of historic Annapolis, connecting Main Street and West Street. St. Anne's Church, located at the center of the circle, showcases stunning Romanesque Revival architecture, and its steeple is visible throughout the downtown area.

   
   
   

   Annapolis Church Circle Christmas Lights

   

   Christmastime on Church Circle

   As you travel around the circle, you'll come upon West Street, also adorned with delightful snowflake lights. This unique and vibrant area, recognized as Annapolis' Arts District, offers art galleries, music venues, restaurants and unique shopping opportunities. Stroll along and take in its lively atmosphere.
   

   

   Holiday Lights on West Street

6. Main Street

   The last part of our walk puts us at the top of Main Street. What a gorgeous view down towards the water. The entire street is lit up with classic colonial holiday cheer with a hint of Maryland Bay vibes.

   
   
   

   Annapolis Main Street During Christmastime

   

   Aqua Al 2 Restaurant on Main Street

   Make sure to check out Snowflake Alley, a perfect place for taking photos. It's situated right across from Chick & Ruth's Delly. Given its popularity, you may need to wait your turn to snap a picture.
   

   

   Snowflake Alley

   Red Red Wine, a restaurant about halfway down Main Street, becomes the Holiday Pop Up Bar known as Jingle Bell Bar. It's a great spot to enjoy a holiday-themed cocktail such as a Gingerbread Old Fashioned, Peppermint Expresso Martini or Hot Spiced Mulled Wine.

   
   

   

   Red Red Wine - Jingle Bell Bar

Holidays in Annapolis Maryland - Christmas Lights Trail

Annapolis is incredible to visit any time of year, but Christmastime is genuinely special. I feel so fortunate to live in this amazing town, full of beauty, history, and community. I encourage you to embark on this Christmas Lights Walking Tour and soak in the cheerful atmosphere.

If you would like some additional information on Annapolis, check out my additional posts listed here!