November brings plenty of reasons to get out and enjoy our communities. From wildlife art in Easton to holiday shopping in St. Michaels and tree lightings by the beach, the calendar is filling up with seasonal traditions.
Whether you’re planning a family outing, a date night, or a weekend with visiting friends, here are 12 events to explore around Annapolis, the Eastern Shore, Ocean City, and coastal Delaware this November 2026.
Annapolis Jazz & Roots Festival
November 6–8 and November 13–15 | Various Annapolis venues
Make a night of it with live music in Maryland’s capital. The Annapolis Jazz & Roots Festival spans two weekends, bringing jazz, roots music, and cultural programs to venues throughout the city.
Pair a performance with dinner downtown for an evening close to home that feels like a getaway.
Explore the festival and performance schedule.
Bay Bridge Run
Sunday, November 8 | Chesapeake Bay Bridge to Kent Island
Here’s a chance to see the Chesapeake from a different perspective. The Bay Bridge Run welcomes runners and walkers for a 10K across the bridge’s eastbound span, finishing on Kent Island.
With sweeping water views and a post-race celebration, this is a memorable way to spend a November morning. Registration and transportation planning are required.
Get registration, parking, and shuttle information.
Waterfowl Festival
November 13–15 | Easton, Maryland
Few events capture the Eastern Shore’s character quite like the Waterfowl Festival. This three-day celebration brings wildlife art, carving, calling championships, demonstrations, food, live music, and family activities to Easton.
Browse the artwork, explore the town, and enjoy a weekend centered on the Chesapeake region’s wildlife, heritage, and conservation.
Plan your Waterfowl Festival visit.
Winterfest of Lights
November 19–January 2 | Northside Park, Ocean City, Maryland
Ocean City’s holiday season sparkles at Northside Park. Winterfest of Lights returns with a walk-through display that makes a festive outing for families, couples, and visiting guests.
November hours are 5:30–9:30 p.m. Look for special experiences, including Fire & Ice nights and pet-friendly Wednesdays.
View Winterfest details and special nights.
Lights & Leashes
November 20–22, 5–9 p.m. | Sandy Point State Park, Annapolis
Bring your four-legged family member along for some holiday cheer. Lights & Leashes offers three special evenings to walk through the Lights on the Bay display before its regular drive-through season begins.
It’s an opportunity to enjoy the lights on foot with your dog while supporting the SPCA of Anne Arundel County.
Learn more about Lights & Leashes.
Eastern Shore Sea Glass & Coastal Arts Festival: Holiday Edition
Saturday, November 21, 10 a.m.–4 p.m. | St. Michaels, Maryland
Looking for a gift with a little coastal personality? Head to the Chesapeake Bay Maritime Museum for the holiday edition of the Eastern Shore Sea Glass & Coastal Arts Festival.
The waterfront event features exhibitors, live music on two stages, food and drinks, and glassblowing demonstrations. It’s a lovely excuse to start your holiday shopping and spend a day in St. Michaels.
Find festival information and tickets.
Lights on the Bay
November 23–January 3 | Sandy Point State Park, Annapolis
Prefer to enjoy holiday lights from the comfort of your car? Lights on the Bay returns with a two-mile scenic drive featuring approximately 70 animated and stationary displays.
This seasonal tradition also benefits the SPCA of Anne Arundel County, adding a meaningful purpose to a festive evening.
Plan your Lights on the Bay outing.
Holiday Shoppers Fair
November 27–29 | Roland E. Powell Convention Center, Ocean City
Trade some of the Thanksgiving weekend shopping rush for a browse through handcrafted gifts and artisan creations.
The 44th Annual Holiday Shoppers Fair opens at 10 a.m. each day, offering a seasonal stop for anyone searching for something special to wrap.
Check Ocean City’s official November event information.
Ice Ice Berlin & Tree Lighting
Friday, November 27, beginning at 5 p.m. | Downtown Berlin, Maryland
Downtown Berlin welcomes the holiday season with more than 30 ice sculptures and its annual Christmas tree lighting.
The tree lights up at 6 p.m., making this a festive way to spend the evening after Thanksgiving. Take a stroll through town and enjoy the seasonal atmosphere.
See Berlin’s official event calendar.
Rehoboth Beach Christmas Tree Lighting
Friday, November 27, 6:30–7:15 p.m. | Rehoboth Beach Bandstand
There’s something especially inviting about holiday lights by the ocean. Rehoboth Beach welcomes the season with holiday music and a countdown to the lighting of its community tree.
Gather at the Bandstand at 1 Rehoboth Avenue for this Thanksgiving weekend tradition.
Find details on the city’s official calendar.
Berlin Merry Marketplace
Saturday, November 28, beginning at 11 a.m. | Berlin Welcome Center
Keep the holiday weekend going with a visit to Berlin’s Merry Marketplace. Browse local art and enjoy roasted chestnuts and hot chocolate at the Welcome Center parking lot, 14 S. Main Street.
It’s an easy addition to a day spent exploring downtown.
View Merry Marketplace information.
Annapolis Grand Illumination
Sunday, November 29 | Downtown Annapolis
Close out November with the glow of Annapolis’s annual Grand Illumination. Families, friends, and visitors gather near Market House and City Dock to welcome the holiday season with the downtown tree lighting.
Make time to enjoy the waterfront and historic streets while you’re there.
Explore Annapolis’s November events.
Find a New Favorite Tradition
A festival, a waterfront walk, or an evening under holiday lights can become the outing everyone looks forward to next year. Pick a date, invite someone along, and enjoy what our local communities have planned.
Thinking about making one of these communities home? I’d love to help you explore the neighborhoods and find a place that fits your next chapter.
Gloria Pruitt
Every Dream Has an Address
Event information reflects published November 2026 schedules. Check the linked organizers’ pages for admission, availability, weather updates, and schedule changes before traveling.
