Did you know that Naptown was named one of the best places to visit during the winter holidays by Travel + Leisure? From Thanksgiving to New Year’s Eve events, there’s always something going on in America’s Sailing Capital. Here are 5 can’t-miss Annapolis holiday events for 2018.

1. Midnight Madness

Annapolis Holiday Events 2

Get your holiday shopping done while immersed in a winter wonderland. On December 6th and 13th, from 6:00 p.m. to midnight, and again on December 20th, from 6:00 p.m. to 11:00 p.m., Downtown Annapolis will gleam with holiday decorations, trees, lights, and snowflakes. Shop local stores along Main Street, West Street, Maryland Avenue, State Circle, and Dock Street during Midnight Madness. All the while, you’ll be immersed in a picturesque scene straight out of a Norman Rockwell painting or Charles Dickens book. Best of all, carolers and other street performers will fill the air with the joyful sounds of the holidays.

2. Lights on the Bay

From November 17th, 2018, to January 1st, 2019, you can take a drive under dazzling Christmas lights along the Chesapeake Bay. Over 60 animated and stationary displays illuminate two miles of roadway during Lights on the Bay at Sandy Point State Park. Now entering its 24th year, this Annapolis tradition is rolling out two new themes: North Pole Village and Enchanted Fairytales. Also, all of the proceeds will go to the SPCA of Anne Arundel County.

3. Chocolate Binge Festival

If just the name has you drooling, make it a point to attend the 4th annual Annapolis Chocolate Binge Festival. On Sunday, December 2nd, from 12:00 p.m. to 5:00 p.m., the first block of West Street becomes home to local chocolate vendors. In addition to the mouthwatering chocolate truffles, cakes, cookies, and other specialties, the festival features family-friendly entertainment and holiday shopping. You can also witness the lighting of the Holiday Light Canopy over West Street and visit Santa. Additionally, make sure to bring toys, coats, and hats for the We Care and Friends holiday drive, which supports local kids in needs.

4. Eastport Yacht Club Lights Parade

On Saturday, December 8th, take a trip to Annapolis Harbor and Spa Creek for the Eastport Yacht Club Lights Parade. From 6:00 p.m. to 8:00 p.m., you can watch as festively decorated boats pass by. Make sure to bundle up in your warmest attire for this family-friendly holiday event. You won’t want to miss seeing all the hard work that the crews put into lighting up the night.

5. City of Annapolis New Year’s Eve Celebration

On Monday, December 31st, you can say goodbye to 2018 and ring in 2019 at the Annapolis New Year’s Eve Celebration. Sponsored by the City of Annapolis, this event kicks off at 3:00 p.m. with kid-friendly activities at Weems-Whelan Memorial Field. Then, at 5:30 p.m., fireworks will be on display for the kids. At 8:00 p.m., adults can continue the party at City Dock. Above all, free live entertainment, dancing, and a midnight fireworks display will happily bring you into the New Year.

Get out and explore the city with Annapolis holiday events. From holiday shopping to New Year’s celebrations, there are plenty of Annapolis holiday events for the whole family. And, while you’re in the area, don’t forget to stop by Cape Ace Hardware to get your home ready for the holidays!