Discover the Best Things to Do in Maryland This Fall and Winter
As the leaves change and the air turns crisp, Maryland comes alive with festivals, outdoor adventures, and seasonal celebrations that are perfect for everyone — from families to foodies, art lovers to thrill seekers. Whether you’re looking to wander through colorful fall foliage, enjoy craft fairs and pumpkin patches, or soak up the holiday magic with festive lights and markets, Maryland has something exciting happening every weekend from October through December.
In this guide, we’ve rounded up over 50 events across the state — from the mountains of Garrett County to the coastal charm of Ocean City, and from bustling Baltimore to the historic towns of the Eastern Shore — so you can plan your perfect fall and winter adventures.
Get ready to mark your calendar and explore the best Maryland has to offer this season!
| Date | Event | Region | Notes |
|---|---|---|---|
| 25-Oct | Halloween/Boo Bash events | Calvert County | Multiple fall/family-friendly events |
| Oct 25-26 | Halloween Eye Spy Trains - Wheaton Regional Park | Montgomery County | Family outing with themed train rides |
| 26-Oct | Rock Hall FallFest | Kent County / Eastern Shore | Art & craft festival centered on oysters |
| 1-Nov | Veteran's 5K / Patriot 5K - Middle River | Baltimore County | Running event for Veterans/Military |
| 8-Nov | Veterans Parade | Baltimore City | Large public parade |
| Nov 8-9 | Telescope Training - Maryland Science Center | Baltimore | Hands-on session with telescopes |
| 12-Nov | The Furious Bongos performing Frank Zappa | Baltimore | Concert event |
| 15-Nov | Mr Trash Wheel 'Dumpster Dive' Volunteer Event | Baltimore | Community environmental event |
| 16-Nov | Toddlergarten: Toddler Math - Science Center | Baltimore | Family-friendly educational event |
| Nov 21-23 | Ocean City Holiday Bazaar | Ocean City | Seasonal shopping and artisan event |
| 28-Nov | Thanksgiving Day Parade | Baltimore | Annual city parade with floats and performances |
| Dec 1-24 | Gaylord National Resort Christmas on the Potomac | National Harbor | Holiday-themed displays and events |
| Dec 1-25 | Enchanted Garden of Lights | Howard County | Light displays and festive entertainment |
| 6-Dec | Silver Bells in the City | Baltimore | Holiday lighting ceremony and performances |
| 13-Dec | Glass Art: Sea Glass Wreath - Maryland Science Center | Baltimore | Interactive craft workshop |
| 15-Dec | Holiday Open House at B&O Railroad Museum | Baltimore | Holiday-themed museum activities and train rides |
| 20-Dec | Nativity Pageant - St. Mary's County | St. Mary's County | Community holiday pageant event |
| Dec 24-25 | Holiday Boat Parade | Annapolis | Decorated boats parade along the harbor |
| Oct 12-13 | Frederick Oktoberfest | Frederick / Central MD | Music, beer, and German cultural festival |
| 19-Oct | Howard County Fall Festival | Howard County | Family festival with games, food, and crafts |
| 31-Oct | Halloween Trick or Treat Trail | Montgomery County | Community Halloween trail with activities |
| 5-Nov | Chestertown Tea Party Weekend | Chestertown / Eastern Shore | Historical reenactments and tours |
| 22-Nov | Rising Tides Festival | Ocean City | Music festival featuring 70s/90s/2000s hits |
| 5-Dec | Winter Lights Festival | Annapolis | Light displays and family-friendly events |
| 7-Dec | Hershey Sweet Lights Experience | Baltimore County | Drive-through holiday light display |
| Dec 12-14 | Poinsettia Holiday Market | Baltimore City | Holiday shopping with local vendors |
| Dec 20-31 | SnowFest | Ocean City | Winter-themed family fun with ice sculptures and snow activities |
| Oct 17-19 | Annapolis Arts Festival | Annapolis | Art fair with local artists and live music |
| Oct 24-25 | Sykesville Heritage Festival | Carroll County | Parade, craft vendors, and family activities |
| Nov 1-2 | Fall Beer & Food Festival | Columbia / Howard County | Local craft beer tasting with food pairings |
| Nov 9-10 | Baltimore Book Festival | Baltimore City | Book signings, authors, and literary events |
| Nov 15-16 | Chestertown Arts & Crafts Fair | Chestertown / Eastern Shore | Local artisans and crafts showcase |
| 1-Dec | Deck the Halls at Historic Ellicott City | Howard County | Holiday-themed historic house tours |
| Dec 6-7 | Holiday Train Show at B&O Railroad Museum | Baltimore | Model train holiday display |
| 12-Dec | National Harbor WinterFest | National Harbor | Seasonal rides, activities, and lights show |
| 18-Dec | Holiday Pops Concert | Baltimore | Seasonal music performance |
| 20-Dec | Frosty Festival | Ocean City | Winter family festival with games and crafts |
| Dec 21-22 | Winter Wonderland Market | Baltimore | Holiday market with local vendors and entertainment |
| Oct 9-10 | Mount Airy Apple Festival | Carroll County | Family-friendly apple festival with games, music and crafts |
| Oct 15-16 | Howard County Pumpkin Festival | Howard County | Pumpkin picking, hayrides and farm activities |
| Oct 20-21 | St. Michaels Fall Festival | St. Michaels / Eastern Shore | Festival with music, crafts and local food |
