If you live in the Mid Atlantic and looking for a road trip idea over the holiday season, how about hitting Annapolis?  Thanks to the tourist board of Annapolis for compiling what are the top places to visit in Annapolis if only given 24 hours.

24 Hours in Annapolis for the Holidays

Day One

Welcome to Annapolis! Because Maryland’s capital city is such a walkable town, you might want to drive directly to your historic bed and breakfast or hotel and park your car. You won’t need it to get around downtown Historic Annapolis!

Annapolis has a wide range of accommodations to choose from. If you’re looking for a waterfront property, the newly renovated Annapolis Waterfront Hotel is a perfect choice. If you have a soft spot for the historic, Historic Inns of Annapolis, the Flag House Inn, Inn and Horn Point, and other Annapolis bed and breakfasts will undoubtedly have just what you’re looking for. If you’re keeping track of your hotel points, Westin Annapolis, Hilton Garden Inn Downtown Annapolis, and the new Graduate Annapolis Hotel are among the Annapolis properties ready to serve you.   

To get the lay of the land, head to the 26 West Street Visitors Center. Its COVID-19 operating hours are Thursday through Sunday, 10:00 a.m. until 4:00 p.m. Visit Annapolis & Anne Arundel County’s (VAAAC) helpful Information Specialists will answer any questions you might have and provide you with a holiday guide that outlines the many in-person and virtual events and activities on tap for this year.

Exploring the nooks and crannies of the brick-lined streets of Historic Annapolis on foot is half the fun. Storefront after storefront is bedecked with green garlands, red ribbons, and white lights – making the city feel every bit like a European town of years gone by.

The boutiques and art galleries of downtown Annapolis are a perfect place to wrap up your Christmas shopping. Main and West Streets, Maryland Avenue, and State Circle are among the many streets that offer one-of-a-kind gifts designed to please everyone on your shopping list. If you’re feeling creative, duck into the Clay Bakers and make your own special gift. Love pottery? Be sure to stop by Annapolis Pottery on State Circle. Have a passion for fine leather?

Visit Hobo Leather Goods’ flagship store. Chances are you’ve seen their purses, wallets, and more online and in some of your favorite department stores. Now’s your chance to take advantage of great deals at their only brick and mortar store. Blanca Flor features silver jewelry and treasures from around the world. Local by Design on Main Street showcases the work of dozens of local artisans.

Be sure to make your way to City Dock. It’s the heart and soul of Annapolis – a place to see and be seen. If you visit after December 1, be sure to check out the city’s Christmas tree. This year, it will be decorated in honor of the United States Naval Academy’s 175th anniversary.

While you’re at City Dock, scan the skyline to see the newly installed Naval Academy dome. Completed in the fall, the copper colored dome replaces the green patina version that adorned the chapel for decades. It’s estimated it will take about 25 years for the new dome to weather to the patina color visitors have come to know. While the Naval Academy is currently closed to the public, be sure to capture a shot of the new attraction on the Annapolis skyline.

Lunch Anyone?

As you’ve made your way around town, you’ve no doubt spotted several al fresco dining options. Outdoor tent dining is available in the many recovery zones that have been set up throughout the downtown. Reynolds Tavern offers dining in your own personal globe-like structure.

Flamant Restaurant in West Annapolis has built a new outdoor dining area that’s open year-round. Top of your lunch with homemade ice cream made on site at the family-owned Annapolis Ice Cream Company. Looking for something savory? Opened in November 2020, Dangerously Delicious Pies will not disappoint.


The holidays are the perfect time to visit Annapolis. Our historic homes are adorned in their finest. Be sure to tour one or more of them during this magical time.

Winter Flowers from Around the World

Daily, except Tuesdays

Noon to 5:00 p.m.

Hammond-Harwood House, 19 Maryland Avenue, Annapolis

Tour the home adorned with floral displays inspired by flowers that bloom around the world in winter, including Winter Jasmine, Snowdrops, English Primrose, and Holly. Created by local garden clubs, the displays celebrate the home’s Decadent Décor: Global Imports in an Early American Port City exhibition which highlights early Annapolis residents’ furnishings from around the world. Reservations required.

Winter Blooms at London Town (car required)

Call ahead for days and hours of operation.

Historic London Town and Gardens, 839 Londontown Road, Edgewater


Enjoy stunning views of South River on a walk through ten acres of woodland and ornamental gardens. Be enchanted by the colorful berries of the Hollies (Ilex sps.) and Viburnum (Viburnum sps.). Take in the sweet smell of Paperbush (Edgeworthia chrysantha). Explore a wide range of evergreen shrubs and ground covers, such as Danae, Rhodea, Pieris, Illicium, and more. The real standouts are the white, pink, and red cold-hardy Camellias (Ackerman hybrids). Check out the Discover London Town exhibit in the Visitor Center and explore reconstructed colonial buildings, including the Lord Mayor’s Tenement and the Carpenter Shop. Enjoy a virtual tour of the National Historic Landmark William Brown House.

If you have the time, be sure to duck into one of the 18 galleries that are within walking distance of one another in downtown Annapolis. McBride Gallery has been gracing Main Street for more than 35 years. The Annapolis Collection Gallery on Gallery Row on West Street showcases the work of the late Charles Emery and Marion Warren.

Beloved by the locals, their black and white photography captures the stories of generations of watermen and the lives of everyday people who made their living on or near the Chesapeake Bay. Be sure to check out the newest gallery in town, 57 West. The new home of the Annapolis Arts Alliance (AAA) opened in August 2020. The “fusion of the arts” features the work of AAA members – paintings in all media, photography, jewelry, sculpture, glasswork, pottery, textiles, mixed media and more.

As you walk along, be sure to take in the history that surrounds you. Keep an eye out for the historic markers on many of the downtown properties. If you’ve picked up a Historic Marker brochure from the Visitors Center, you’ll be able to identify the centuries of architecture that surrounds you – including the five-part brick Georgian mansions that Annapolis is known for. The William Paca House, Hammond Harwood House, Chase-Lloyd House, and Brice House are great examples of this stunning architecture.

Time for dinner

If antiques are on your shopping list, you may well find yourself on Maryland Avenue – a hit with the locals and a great find for the discerning shopper. After you’ve stopped in Evergreen Antiques and True Vintage and Blue Crab Antiques, you may want to settle in at Galway Bay for dinner and their famous Irish Eggnog.

The restaurant imports its proprietary blend from Ireland each year. It’s a favorite with the locals who race to purchase cases for gifts as soon as word’s out that the holiday supply has arrived. Locals know if they don’t buy it quickly, they may have to wait until next year.

For the first time this year, Galway Bay is introducing its new Irish Eggnog ice cream made exclusively for Galway Bay by Annapolis Ice Cream Company. You must be 21 years old to purchase it! Galway Bay also features the largest selection of Irish Whiskey in Maryland.

A host of al fresco dining options awaits you in downtown Annapolis and Eastport, home of Annapolis’s Restaurant Row. If you prefer, take advantage of a myriad of carryout dining options you can enjoy back at your hotel or historic bed and breakfast.

Evening Fun

Depending on the day that you visit, there are any number of appealing evening activities to choose from:

Lights on the Bay

Friday, November 20 – Saturday, January 2

5:00 p.m. to 10:00 p.m.

Sandy Point State Park, 11 East College Parkway, Annapolis


This spectacular drive-through holiday lights show beside the Chesapeake Bay features more than 70 animated and stationary holiday and children’s displays, including traditional Maryland-themed favorites. Proceeds benefit SPCA of Anne Arundel County.

Midnight Madness Holiday Shopping

Thursdays, December 3, 10, and 17

December 3 and 10, 4:00 p.m. to midnight

December 17, 4:00 p.m. to 11:00 p.m.

Downton Annapolis


Enjoy outside musical performances as you stroll along Main and West Streets, Maryland Avenue, State Circle, and Dock Street in search of that perfect gift. Check out Snowflake Alley, the holiday lights canopy over West Street, and the Christmas tree at Market space as you shop to support local businesses.

Holiday Candlelight Stroll

Fridays and Saturdays, December 4-26; Sunday, December 27

7:00 p.m. to 9:00 p.m.

Tour departs from Market House Park, Annapolis


Glowing lanterns light your way as you stroll along the centuries-old brick lined streets of Maryland’s capital city adorned for the holidays. A period-attired guide will share holiday traditions of times past against the backdrop of colonial mansions, Victorian homes, and quaint shops.

Jolly Express Cruise

Friday-Sunday, December 4-27

6:00 p.m., 7:00 p.m., 8:00 p.m.

45-minute cruise departs from City Dock, Annapolis


Hop aboard Miss Anne, all decked out for the Holidays, for a Spa Creek “sleigh ride” on the Jolly Express with Captain Santa at the helm. Miss Anne will be adorned in reindeer spirit for an intimate cruise that includes hot cocoa, holiday music, and good cheer. Bring your own blankets!

Holiday Stroll & Cruise

Saturdays and Sundays, December 5-27

1:30 p.m. to 3:30 p.m.

Tour departs alternately from slip #2 at City Dock and Market House Park


Enjoy stories of holiday traditions mingled with classic colonial tales as you stroll the charming streets of Historic Downtown Annapolis with your period-attired guide. Afterwards, your guide will bring you to City Dock to enjoy a 40-minute Spa Creek cruise aboard the festively decorated Miss Anne.

Captain Santa’s Cruise

Saturdays and Sundays, December 5-27

4:00 p.m. to 4:40 p.m.

Tour departs from City Dock


Your whole family will enjoy this cruise complete with cheery holiday music and Santa himself giving out candy canes.

Eastport Yacht Club Lights Parade

Saturday, December 12

6:00 p.m. to 8:00 p.m.

Annapolis Harbor and Spa Creek


More than 30 brightly lit boats bedecked for the holiday season parade around the Annapolis waterfront and Spa Creek during the popular annual event. Thousands of lights and a host of jolly revelers make this a fun Christmas tradition for the entire family.

At day’s end, it’s nice to know you can walk back to your historic bed and breakfast or hotel and call it a day.

Day Two Holiday Visit in Annapolis


Enjoy breakfast at your bed and breakfast or hotel or check out some of the local restaurants. Feeling patriotic? Head to Chick & Ruth’s Delly to recite the Pledge of Allegiance at 8:30 a.m. Monday-Friday or 9:30 a.m. on weekends. It’s never too early to enjoy one of their famous milkshakes! Hungry? Try Iron Rooster’s chicken and waffles – a big hit any time of the day! While you’re there, treat the family to homemade “RoosTarts,” made fresh every day! Miss Shirley’s is another breakfast tradition that’s filled with wholesome Chesapeake Bay goodness.

If shopping kept you plenty busy yesterday, be sure to walk by the Maryland State House today. While the oldest State House in continuous legislative use in the nation is closed to the public right now, it’s a grand building to see. It was here that George Washington resigned his commission as commander in chief of the continental army and the Treaty of Paris was ratified, officially ending the Revolutionary War. Nestled on State Circle, the State House is just across the street from Annapolis Pottery – a perfect place for picking up an Annapolis memory. The third oldest college in the nation – St. John’s College is just footsteps away. Be sure to walk the campus grounds. They’re beautiful any time of the year!

No stay in Annapolis is complete without a visit to the home and Garden of Declaration of Independence signer William Paca.

Colonial Annapolis Holiday

Friday, November 13 – Sunday, December 6

Friday-Saturday, 11:00 a.m. to 4:00 p.m.; Sunday, Noon to 4:00 p.m.

William Paca House and Garden, 186 Prince George Street, Annapolis


Celebrate the Season at the William Paca House where William, Mary, and the household servants have prepared for the festive season. Experience the holidays as docents lead you through the first floor of the house decorated in true colonial fashion.

Enjoy a virtual tour of the entire house and a docent led tour of the 2-acre William Paca Garden. Last guided tour departs at 2:00 p.m. Last entry for self-guided tours of the garden and a virtual tour of the house is 3:30 p.m. Reservations required for the docent-led tours.


If you have time, enjoy a final al fresco lunch at Market Space or arrange for carryout to enjoy on the journey home.

Until Next Time!

Annapolis and Anne Arundel County are brimming with fun holiday experiences for the whole family to enjoy. Since you can’t possibly take advantage of all there is to do in 24 hours, be sure to come back to enjoy the magic of the holidays in the days ahead.