Winter Journey to Annapolis

When it comes to the seasons, we believe there are two types of people in the world: ones who prefer to spend their winters in warm tropical places sitting by a pool and drinking margaritas, and those who prefer the winter wonderland that is Annapolis! If your journey takes you to the cold and the wintry, this guide will help make sure you experience all the best things to do in Annapolis in winter!

Day 1

Whether you traveled a long way or live relatively close to Annapolis, this first day is all about recovery and exploration as you unpack your bags, open cupboards, and fall in love with a house for the first time in your life. A relaxing and renewing dinner at Cooper’s Hawk Winery & Restaurant will help you forget the stresses of your day on the road. Located at 1906 Towne Centre Boulevard, it’s not just the Bourbon Lacquered BBQ Pork Chop that will bring a smile to your face; the extensive wine menu will be the perfect welcome to our idyllic Chesapeake Bay town.

Day 2: Refreshed & Renewed

After a deep and restful sleep, you will awaken eager to experience the wonders of Annapolis in the winter, and your first full day in town promises to be a fulfilling one. The day will be cool and brisk, and if you’re visit takes place during the holidays, the Nutcracker Ballet is first on the schedule! Beautifully performed by the Ballet Theater of Maryland, today’s journey will have you falling in love with the world of dance. It’s defeinitely one of the best Annapolis winter activities!

Day 3: Annapolis Maritime Museum, 723 2nd Street

A journey into the past is always fascinating and is even more so when you spend your 3rd day in town at the Annapolis Maritime Museum. Dedicated to the preservation of the ecology of our town, the exhibits found here will deepen your understanding of life on the water. Featuring skipjacks and oyster tanks, cannons and crab pots, your winter journey will be enhanced by a visit to this worthy museum—and you’ll be able to stay a little warmer as well!

Day 4: The Perfect Cup of Cocoa

As the temperatures drop and we journey deeper into the winter months, the search for the perfect cup of cocoa becomes a mission in earnest! Knowing how difficult it can be searching for anything in a new place, we have done the research for you, and Annapolis’ winner is the Annapolis Ice Cream Company. Located at 196 Main Street, the rich and creamy beverage served here is a welcome treat after a chilly walk through the historic district of Annapolis. If you’re looking for things to do in Annapolis in winter, make sure you visit the Annapolis Ice Cream Company!

Day 5: Discover Your Inner Peace

The iconic brick building of St. Anne’s Church found at 199 Duke of Gloucester Street has been a comfort to residents and tourists for almost three centuries. Originally constructed in 1704 and undergoing multiple renovations, restorations, and even a rebuild or two since, it is still a place designed to help you find your inner peace. The stained glass windows never fail to please and the free tours fit into any vacation budget.

Day 6: Building a Fire

Hot cocoa isn’t the only part of winter designed to keep you warm. Down coats, thick woolen socks, and a roaring fire in the fireplace help keep the chill of the season away. And when you choose to stay home on this last day of your journey, our At Home Annapolis homes with fireplaces will chase away the most determined chills. Spend the day snuggled onto the couch watching old movies on the big screen, reading a good book in that overstuffed chair by the window, and fixing a winter feast. Chili always warms the soul, and you can get all the ingredients from Graul’s Market at 607 Taylor Avenue.

Day 7: It’s Not Goodbye

Goodbyes are so final, and even though this is your last day in Annapolis, we like to think that your life’s journey will bring you back again. It’s never too soon to start making plans for your next getaway to experience all the things to do in Annapolis winter!—reserve yours today!

(443) 837-6870