The holiday season is officially here and we’re ready to help you celebrate. Join us at the Annapolis Town Center where you’ll have plenty of chances for the whole family to have fun and build lasting memories. Experience the season as you do all your gift shopping, decorating, and take in other magical activities and traditions. This year, we’re putting a twist on our usual holiday gatherings, and trust us, you won’t want to miss it!

Tree Lighting

Celebrating the Holidays may look a bit different this year, but some traditions remain. This year, our 12th annual Annapolis Town Center Tree Lighting Ceremony on November 21 will offer you the chance to experience the holiday magic and celebrate safely with one of two ticketed holiday events:

Holiday Vinyls & Vino

November 21 | 5:00 – 7:00 pm

With the help of our friends from Vintage Views: A Wandering Bar and DJ Crawdads, guests will enjoy a front-row seat to Santa lighting the Christmas Tree. For just $20, ticket holders can enjoy a fun evening of wine cocktails, graze boxes, and sweet boxes, all while taking in the magic of the season. Plus, each ticket includes one complimentary glass of holiday wine. Space is limited.


Drive-in Movie Featuring Dr. Seuss’ The Grinch

November 21 | 5:00 pm

We all have our own list of must-watch holiday movies to help welcome in the season. Bring the whole family out for a viewing of Dr. Seuss’ The Grinch at our drive-in movie lot. A $50 ticket gives you entry to the movie, a complimentary popcorn bucket, and a live stream of the annual Tree Lighting prior to the show. You’ll even get a visit from Santa himself! Space is limited.


Holiday Stroll

November 28

In support of Small Business Saturday, the Annapolis Town Center is happy to host our first-ever Holiday Stroll on November 28. Enjoy an eventful day that will surely get you in the spirit! Sip and shop as our retailers open their doors and bring the shopping experience to the sidewalks, conveniently creating a holiday market. Get crafty during a wreath-making workshop on the Green hosted by The Chesapeake Wreath Company. Easily find the right gift for your loved ones from one of our women-owned businesses and guest pop-up shops like Scout & Molly’s, Sit. Stay. Play., and Beautifully Wilde Boutique Mobile Airstream. And, adding to the holiday magic – pick up your perfect tree for the season at the Town Center’s own Christmas Tree Lot in partnership with Whole Foods!

Make sure a trip to the Town Center is part of your plans for this holiday season. There are more events coming your way, so follow us on Facebook and Instagram for regular updates on events and happenings.

It’s beginning to feel a little eerie, spooky, and downright frightful! 

This October, join us for Fright Nights at Annapolis Town Center. Enjoy five nights of chills, thrills, and fun. Grab the entire family, a group of friends or that special someone as you head over to the Haunted House located near The Green to check-in, grab your concessions and head out for your gripping experience. 

First, you will be guided in the direction of a spooktacular drive-thru Haunted Alleyway Experience, complete with all the chilling scares you come to love this time of year. Then, mosey down the fog-filled path as you park to wait for your favorite fall feature film at the drive-in movie. It is the perfect night out for all ages while still keeping your health and safety in mind!

Here is our movie line-up:


Joining us during an Adults-Only night? Pop by the beer garden hosted by Vintage Views: A Wandering Bar prior to the start of the movie for a few drinks and live music by DJ Crawdads. As part of your ticket, you will receive two complimentary drink tickets to the beer garden! Our restaurants will also be ready and available for curbside pick-up for you to enjoy dinner and a movie! Need a photo op? We have you covered there too. Just behind the big screen, you will find fun photo stations for everyone to enjoy.

Stay tuned to our social channels leading up to the events for special giveaways where you could win tickets to one of the featured Fright Nights. Don’t want to risk missing out? Purchase your tickets today for this haunting good time.