November 15, 2023
Becca Kraybill
|
Contributor
The holidays are just like dessert—fun and tasty, but pacing is key. We've rounded up the area’s many holiday events so you can stay focused on the good stuff. Bookmark, share with friends, and most importantly have fun and happy holidays!
Please note we will be updating this list often as the holidays progress.
Table of contents:
Head to Sandy Point State Park to drive through 2 miles of light displays (over 70 of them!) with the amazing backdrop of the Chesapeake Bay Bridge. Displays range from classic holiday scenes to Annapolis-inspired scenes.
Admission is $20 per car or $30 for large passenger vans, mini buses, and trolleys. Big buses are $50 each. 3D glasses are available for $5 a pair. You can buy tickets online. Lights on the Bay is open daily from November 19 through January 1.
Proceeds from Lights on the Bay support SPCA, the largest animal welfare nonprofit in Anne Arundel County.
Join Annapolis Town Center at 5 PM on December 7 to light the first candle on a giant Menorah in celebration of Hanukkah. The Menorah is located across from J. Alexander’s Restaurant.
What started as one man decorating his boat and cruising down Ego Alley has turned into not just one of Annapolis’ favorite events, but America’s. USA Today routinely includes the Eastport Yacht Club Lights Parade in its list of best holiday parades in America. December 9 from 6–8 PM. Read our Insider's Guide for maximum enjoyment.
The first three Thursdays in December are Annapolis’ best shopping days of the year. Shops stay open late, carolers sing, and many shops serve refreshments – some even have alcohol. Oh, and there are alpacas on Main Street. It’s a Norman Rockwell-Charles Dickens charm you won’t find anywhere else.
4 PM to midnight on December 7 and 14. Shops close at 11 PM on December 21. Shops on West Street, Maryland Avenue, Main Street, and Market Space participate.
Returning for its second year. The market features over 100 artisans and vendors and is only open for four days at City Dock. Sip on hot chocolate and adult beverages while you shop from December 7 through 10.
Hours:
Malls have always been the classic Santa photo spot and this year is no exception. Westfield’s own little North Pole is across from Free People. Lines get pretty long on weekends and Westfield knows keeping kids calm is a tall order so there are activities available once inside.
Reservations are recommended – especially on weekends. Click here to make one. Open from November 10 to Christmas Eve.
P.S. Show this reel for $5 off your Santa package. Monday–Thursday only.
Step into Santa’s Cottage for a photo op with the legend himself. Reservations are encouraged and walk-ins are welcomed. If you’re booking online, you must deposit $20 for time with Santa and credit toward a digital purchase. Photo packages range from $37-$47.
Hours vary (and Santa takes well-deserved breaks) so check times here. Open November 18 through December 23.
Homestead Gardens is pretty much Christmas central. With live & artificial Christmas trees, legendary train sets, seasonal plants, and pretty much any decoration you could ever want, it’s no surprise Homestead Gardens offers photos with Santa as well.
Photo sessions are available at both locations (Severna Park & Davidsonville) November 25 through December 17 and reservations are required. Registration opens for each weekend at 10 AM on the preceding Monday. Click here for reservations.
Note: You’ll need to take your own photos here.
The star of our 2022 holiday candle collaboration with Annapolis Candle Company that raised almost $10,000 for the Anne Arundel County Food Bank. It's an adorable, old-school place to get your tree.
Address: 31 Old South River Rd, Edgewater, MD 21037
Hours: Check their Facebook
Phone: (410) 353-8919
Eastport's favorite local produce stand becomes Eastport’s most convenient place to get a Christmas tree once it gets cold.
Address: 921 Chesapeake Ave, Annapolis, MD, United States, Maryland
Hours: 10 AM–6 PM daily except weekends (when they open at 9. Sunday closes at 5 PM)
"The Little Nursery on the Left" as they call it. A great local spot to get a Christmas tree. The most convenient place to get a Christmas tree if you live in or near Bay Ridge.
Address: 1120 Bay Ridge Rd, Annapolis, MD 21403
Hours: Monday-Saturday: 7–5 PM | Sunday: 8–3 PM
Phone: (410) 267-0669
As described above, Christmas Central. With locations in Davidsonville and Severna Park and a massive selection of real and artificial trees, you can’t go wrong with Homestead Gardens.
Davidsonville address: 743 W Central Ave, Davidsonville, MD 21035
Severna Park address: 522 Ritchie Hwy, Severna Park, MD 21146
Hours: 9 AM–7 PM daily except Saturday (8 PM) and Sunday (6 PM)
Davidsonville phone: (410) 798-5000
Severna Park phone: (410) 384-7966
This is a cut-your-own Christmas tree farm featuring Fir, Pine, and Spruce Christmas trees. If you prefer pre-cut, they have real trees up to 12 feet tall. Credit cards accepted. Bathrooms on site. Leashed pets allowed.
Address: 6950 Old Solomons Island Rd, Friendship, MD 20758
Hours: 9–4:30 PM on Sat/Sun, 1–4:30 PM on weekdays
Phone: (301) 855-5756
Email: friendshiptrees1@aol.com
Immerse yourself in the holiday spirit with this cherished rendition of The Nutcracker by Ballet Theatre Maryland. Evening showings on December 9 and 16, matinee showings on December 10 and 17. Get tickets.
Annapolis Symphony Orchestra’s signature holiday performance. It features a dozen classic holiday songs performed by Annapolis’ best symphony musicians. December 17 at 7:30 PM. Get tickets.
Classic Theatre of Maryland is living up to its name with two holiday classics on the marquee this season. Performances for both shows run all the way through Christmas Eve.
Get tickets for White Christmas.
Get tickets for A Christmas Carol.
Homestead Gardens has one of the best model train displays you’ll ever see. It fills up an entire shipping container when it's not on display. Trains run at both the Davidsonville and Severna Park locations through December 30. Hours below.
🚂 Davidsonville (pictured)
🚂 Severna Park
The world-famous Budweiser Clydesdales are heading to Annapolis for the Military Bowl Parade. But what many people don’t know is that the magnificent horses (and their Dalmatian buddies) will prance around West Annapolis the day before.
Be on Annapolis Street from 1–4 PM to join the fun.
Pro tip: Seeing the Clydesdales requires some patience. In our experience, this rarely happens right on schedule.
Virginia Tech faces Tulane in the GoBowling Military Bowl at Navy-Marine Corps Memorial Stadium at 2 PM on December 27. Tickets are available from around $35 but this isn’t just for football fans. There’s a parade that steps off from City Dock around 10 PM and marches all the way to the stadium. And who else is leading the parade but the Budweiser Clydesdales?
.png)
Captain Santa takes the helm of Watermark’s Miss Anne for a festive evening cruise on Spa Creek. It’s a 45-minute “sleigh ride” including hot cocoa, holiday music, and good cheer. A portion of the proceeds will be donated to Historic Annapolis. Runs November 24 through December 31. Get tickets.
You haven’t lived until you’ve seen a large crowd of speedo-wearing Santas running through Downtown Annapolis. Join the fun as a spectator or runner on Saturday, December 16 at O’Brien’s. Registration opens at 11 AM. The run starts at 12:30 PM. Don’t miss the afterparty with Timmie Metz and Tambo.
Annapolis is shooting fireworks over the harbor at two times on December 31. The first will be a family-friendly 7 PM. The second will be the traditional midnight fireworks. If you plan to watch from your boat, arrive early. The 1,000-foot safety zone around the fireworks barge covers the entire width of Spa Creek so you won't be able to boat through between 4 PM – midnight.
Annapolis is once again offering 2 hours of free parking for downtown meter & kiosk parking spots. They’re also offering 1 free hour in the brand new Hillman Garage. Enter the code ParkDTA on the ParkMobile app to access both discounts. The discount works from Thanksgiving to New Year’s Day.
Share this story with your neighbors
We're that funny, deal finding, hip and relevant friend you wish you had. And we'll email you all the Annapolis news and events every weekday morning. For free.
© 2022 Waffle Cone LLC
All Rights Reserved