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2026 Greater Severna Park Fall and Holiday Events Guide
The Jen Holden Group’s Local Guide
2026 Greater Severna Park Fall and Holiday Events Guide
Fall festivals, markets, family outings, and holiday traditions in Severna Park, Arnold, Annapolis, and nearby communities.
Fall around Severna Park tends to arrive one good weekend at a time: a school carnival, a county fair evening, a corn maze afternoon, a cool walk on the B&A Trail and, before we know it, holiday lights on the water. We pulled the dates into one place so you do not have to hunt through a dozen calendars every time the weather turns nice.
This guide covers Severna Park, Arnold, and nearby parts of Anne Arundel County, including Pasadena, Gambrills, Crownsville, Annapolis, Galesville, and Shady Side. Bookmark it and check back. We will keep adding events and updating times, ticket links, and rain plans as organizers release them.
September 2026
Maryland Seafood Festival
through | Sandy Point State Park, Annapolis
Start the season on the Chesapeake with seafood from local vendors, live music, artisans, cooking and eating contests, skipjacks, and activities for kids. Children 12 and under are admitted free. Adult ticket prices vary by purchase date, so check the current ticket page before heading out.
Event details and ticketsMaryland Corn Maze
through , select days | 389 Gambrills Road, Gambrills
This year’s eight-acre maze has a toy theme, plus hayrides, a petting farm, pumpkins, ziplines, slingshots and plenty of games. Tickets are $17.95 online and $19.95 at the gate at the time of publication.
Dates, hours, and ticketsAnne Arundel County Fair
through | Anne Arundel County Fairgrounds, Crownsville
The county fair is five days of animals, exhibits, carnival rides, tractor pulls, pig races, food, and live entertainment. Admission varies by day, and children aged 9 and younger are free.
Fair schedule and admissionCorn-Hooley & Shamrock Shenanigans Festival
| 161 Ritchie Highway, Severna Park
A close-to-home Sunday with cornhole, a free car show, food and drinks, raffles, children’s activities and live music. Check the organizer page for competition registration and the latest schedule.
Organizer detailsSeverna Park Elementary Fall Fest
| 6 Riggs Avenue, Severna Park
A neighborhood favorite with inflatables, carnival games, a DJ and live music, food, raffles, and a silent auction. Admission options range from $10 to $35.
Fall Fest informationKunta Kinte Heritage Festival
| Navy-Marine Corps Memorial Stadium, Annapolis
The 36th annual festival celebrates African American art, culture, history, and community, with special attention this year to the 50th anniversary of Roots. RSVP and program information are available from the organizer.
Festival detailsWest Annapolis Oktoberfest
| Annapolis Street, West Annapolis
A free street festival with local food and beer, music, shopping and vendors. It is an easy one to pair with brunch or a stroll through the neighborhood.
City event listingOctober 2026
Maryland Renaissance Festival
Weekends through , 10 a.m. to 7 p.m. | Crownsville
The 2026 season marks the festival’s 50th year. Expect jousting, stage shows, crafts, food, and a full day inside Revel Grove. October dates are 3–4, 10–11, 17–18 and 24–25. Tickets are required, and popular weekends can sell out.
2026 dates and ticketsGalesville Maritime Heritage Festival
| Galesville
This free, rain-or-shine waterfront festival celebrates the village’s working-waterfront history with a boat parade, boat tours, maritime demonstrations, local seafood, live music and children’s activities. Parking is free.
Festival detailsAnnapolis Pride Parade and Festival
| Annapolis
A colorful community celebration with a downtown parade and festival programming. Check the event page for the final route, stage schedule, and day-of details.
Pride 2026 informationLifeline 100 Community Bicycle Event
| Kinder Farm Park, Millersville
Choose from 15-, 30-, 65- and 100-mile rides, or bring younger riders for the family bike rodeo and bike safari. Registration and route details are available through Anne Arundel County.
County event pageThe Great Annapolis Pumpkins
Beginning just after the first weekend in October | Downtown Annapolis
A handful of real giant pumpkins, some weighing more than 1,000 pounds, turn downtown into a free outdoor photo walk. The 2026 locations are still to be announced. The pumpkins are traditionally carved on the Friday before Halloween.
Follow the 2026 location updatesProvidence Harvest Bash: Passport to Italy
| Providence Greenhouses, Arnold
This is the dressed-up option on the calendar, an adults’ evening supporting Providence of Maryland. Tickets are $250 and include an Italian-inspired celebration at the greenhouses.
Event and ticket detailsFall Harvest Festival and War of 1812 Remembrance
| Hancock’s Resolution, Pasadena
Spend the holiday outdoors with music, crafts, games, artillery demonstrations and period drills at the historic farmstead. Admission is $10 per car or $5 per person.
County event pageHimmel’s Famous Fall Festival
through , 10 a.m. to 3 p.m. | 4374 Mountain Road, Pasadena
Free admission, a moon bounce, crafts, food, and local vendors make this a relaxed stop for families. Check the daily details before going.
Festival informationArt @ the Park
and , 10 a.m. to 4 p.m. | Quiet Waters Park, Annapolis
Artists, demonstrations, live music, food and activities for children fill one of the county’s prettiest parks. Festival admission is free; the park vehicle fee is $8.
County event pageCaptain Avery Oyster Festival
| Captain Avery Museum, Shady Side
A waterfront day built around local oysters, food, music and community. The museum is the best source for ticket, parking and program updates.
Oyster Festival detailsWine Festival at Kurtz’s Beach
| Kurtz’s Beach, Pasadena
Sample Maryland wines while browsing artisans and food vendors and listening to live music along the water. General admission tasting tickets are $45 through October 5 and $50 beginning October 6; non-taster tickets are $20.
Tickets and festival detailsTrick or Treat Trail
| Downs Park, Pasadena
Children age 12 and younger can follow the park’s trick-or-treat route. Advance online registration is required, and regular park gate fees apply.
Registration detailsSevern Christian Fall Fest
| 8132 New Cut Road, Severn
This free community festival packs in tractor and pony rides, a petting zoo, inflatables, a carnival ride, games, a photo booth, food and coffee.
Fall Fest detailsGalesville Fall Festival and Pet Parade
| Galesville Museum
Bring the family, and the dog, for an old-fashioned neighborhood festival and pet parade at the museum. Watch the organizer page for final participation details.
Museum calendarSt. John Oktoberfest
| St. John the Evangelist, 689 Ritchie Highway, Severna Park
An adults-only Oktoberfest close to home. The $35 ticket includes snacks, beer, wine, soda and water.
Event details and ticketsShoptoberfest
| Park Plaza, Severna Park
Park Plaza fills with local vendors for this free fall festival. Children can trick-or-treat and join the costume fun while grown-ups browse and support Severna Park businesses.
2026 event overviewAnnapolis Porchfest
| Murray Hill, Annapolis
More than 25 musicians perform from neighborhood porches during this free, walkable music festival. The rain date is Sunday, October 25.
Porchfest informationA simple fall outing: the B&A Trail
Late October into early November is usually a beautiful window for fall color on the Baltimore & Annapolis Trail. The paved stretch through Severna Park and Arnold works well for bikes, strollers, and leashed dogs, and it is an easy plan when you want to get outside without committing to a ticketed event. Peak color always depends on the weather, so think of this as a flexible weekend option rather than a date on the calendar.
Halloween
Halloween falls on this year. Neighborhood plans and trick-or-treat hours vary around Severna Park, Arnold and Pasadena, so check your HOA, community association or neighborhood group before making the rounds.
November 2026
Y Turkey Trot Charity 5K
| Greater Annapolis Y, 1209 Ritchie Highway, Arnold
The Thanksgiving morning run supports the Y’s work providing food and financial assistance in the community. The Arnold start time and 2026 registration details were not yet posted when this guide was updated, so use the Y link below for the final schedule and packet-pickup information.
Y Turkey Trot updatesSmall Business Saturday
| Severna Park, Arnold, and Annapolis
Make a day of shopping close to home. Park Plaza is a good place to start in Severna Park, and downtown Annapolis businesses traditionally join in with specials and extended holiday energy. Check individual businesses for hours and offers.
Downtown Annapolis shopping informationDecember 2026
Midnight Madness in Downtown Annapolis
Thursdays, , and , beginning at 4 p.m. | Downtown Annapolis
Downtown shops stay open late while carolers, musicians, and other performers bring the streets to life. Shopping continues until midnight on December 3 and 10, and until 11 p.m. on December 17. Calvert Street Garage is free from 6 p.m. to 6 a.m., with circulator buses and shuttles serving downtown.
Midnight Madness and parking detailsGreater Severna Park Holiday Tree Lighting
| Severna Park
The Greater Severna Park and Arnold Chamber of Commerce has its annual Holiday Tree Lighting on the calendar. The start time and full 2026 program are still pending, and we will update this listing when they are announced.
Chamber events calendar44th Annual EYC Lights Parade
| Annapolis Harbor and Spa Creek
Dozens of boats covered in thousands of lights parade through Annapolis Harbor for one of the area’s best-loved holiday nights. Arrive early for a waterfront viewing spot and dress for a cold evening by the water.
Spectator informationHelp us keep this list growing
Do you know of a fall festival, neighborhood tradition, school event, or holiday happening we should add? Send it our way. We live and work here too, and this is the kind of list we save for ourselves, share with friends, and keep checking as the season fills up.
The Jen Holden Group of Compass | Local real estate guidance for Severna Park, Annapolis, and the surrounding communities
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