By Makayla Cropper
November in Annapolis is filled with creativity, culture, and coastal holiday spirit. From vineyard tastings in Davidsonville to lantern-lit tours in historic Downtown, every corner of Anne Arundel County has something happening this month.
November in Annapolis and Anne Arundel County is that perfect blend of cozy, coastal charm and early holiday excitement. Here’s your guide to things to do in Annapolis this November, sprinkled with holiday magic toward the end.
Collectors Tour & Tasting at The Vineyards at Dodon
November 1, 2, 8, 9, 15, 16, 22, 23, 29, 30
The Vineyards at Dodon, Davidsonville
Enjoy an immersive vineyard experience with a guided tour through the cellar and barrel room. End the visit with a seated tasting of Dodon’s limited-edition wines paired with local cheeses and charcuterie all finished with their signature fortified wine, Salute the Truth.
CP Presents Dracula: A Comedy of Terrors
November 1–15
College Parkway Playhouse, Anne Arundel County
Laugh your way through the Transylvanian darkness with this witty, horror-comedy twist on the classic vampire tale. Evening and matinee shows available.
Painting with Nature: Art Workshop
November 2
Davidsonville Family Recreation Center, Davidsonville
Hosted by the Muddy Creek Artist Guild, this hands-on art workshop invites you to create nature-inspired stamps and paint with acrylics. No art experience required, just creativity!
First Sunday Arts Festival
November 2
West Street & Calvert Street, Downtown Annapolis
Explore 125+ vendors featuring fine art, jewelry, photography, pottery, and more in the heart of the Annapolis Arts District. Local food, live music, and good vibes included.
Mr. Paca’s Garden Storytime: “Federico and the Wolf”
November 4
William Paca House & Garden, Annapolis
Perfect for families! Kids ages 3–7 can enjoy story time, crafts, and garden adventures in this charming Colonial garden tucked into the Historic District.
Fall into the Holidays Sip n Shop with Thyme + Stain
November 6
Thyme + Stain, Annapolis, MD
Toast the start of the holiday season with friends, bubbles, and coastal-inspired gifts. Browse beautifully curated home décor and seasonal finds.
Annapolis Jazz & Roots Festival
November 7–16 (Weekends)
Multiple Venues across Annapolis & Eastport, MD
Celebrate local and global sounds with a multi-day lineup of jazz and roots music throughout the city. Most performances are free, but reservations are encouraged.
Darkness to Light – Annapolis Symphony Orchestra
November 7–8
Maryland Hall for the Creative Arts, Annapolis, MD
Enjoy Sibelius’ haunting Swan of Tuonela and other works in a breathtaking orchestral performance inspired by Finnish mythology.
Illuminate Annapolis: Mind-Body-Spirit-Arts Festival
November 8
Annapolis
Explore holistic wellness and creativity at this free festival featuring intuitive readings, energy work, body therapy, handmade jewelry, and workshops for all ages.
Opening Reception: “Groovy” Art Show
November 8
Open Eye Gallery at Arundel Lodge, Edgewater
Enjoy 70’s theme music, food and decorations as you browse, and feel free to wear your grooviest 70’s attire. The first 100 guests will receive party favors!
Naptown Flea Market
November 9
Downtown Annapolis
A curated mix of vintage clothing, handmade goods, records, art, and collectibles. Shop small and enjoy live local music by the waterfront.
Bay Bridge Run
November 9
Chesapeake Bay Bridge, starting near Annapolis
Run (or walk) across the scenic Chesapeake Bay Bridge for a one-of-a-kind experience. The views alone are worth the miles.
Annapolis Gingerbread House Contest & Exhibit
November 22–December 19
Downtown Annapolis
Kick off the holiday season with sweet creativity! Local bakers and artists showcase their most imaginative gingerbread designs in this family-favorite display.
Watermarks Holiday Candlelight Tour
November 29–30
Historic Downtown Annapolis
Step back in time on a guided, lantern-lit walking tour through colonial and Victorian-era Annapolis. Learn about holiday traditions of the past and take home festive treats (including George Washington’s eggnog recipe!).
Motown & More: A Holiday Celebration
November 29th
Maryland Hall for the Creative Arts, Annapolis, MD
Groove into the season with smooth harmonies and soulful renditions of Motown classics and holiday hits from top local vocalists.
Lights on the Bay at Sandy Point State Park
November 23rd – January 1st
Sandy Point State Park, Annapolis
Drive through miles of glowing displays set along the Chesapeake Bay shoreline. A beloved Annapolis holiday tradition for families and visitors alike.
Grand Illumination – Tree Lighting
November 30
Market Space & City Dock, Downtown Annapolis
Watch Downtown Annapolis light up for the holidays during this festive evening of music, treats, and seasonal cheer.
About the Author: This calendar courtesy of VisitAnnapolis.org. It was compiled by Makayla Cropper who has been proud to call North Anne Arundel County, Maryland, home for many years, a fact that makes her an official local.