I know I’m not alone in feeling like summer flew by far too quickly, and autumn is arriving sooner than expected. Believe it or not, many local farms are already opening this weekend, fall festivals are getting underway, and even trunk-or-treat events are beginning to appear on the calendar. To help you stay ahead of the season, I’ve put together a lengthy list of upcoming fall events and activities. And this list will continue to grow as October approaches! Be sure to check back frequently, as this article will be updated regularly with new events, dates, and details.
FALL FESTIVALS & COMMUNITY EVENTS
- Aug 29-Oct 25 (Weekends) All Day: MD Renaissance Festival in Annapolis- $
- Sept 4 – 10AM: Fall Festival at Rolling Acres Farms – $
- Sept 5 – 10AM: Tots in the Front Yard at Leonardtown Library- FREE
- Sept 5 – 5PM: End of Summer Bash at Leonardtown Wharf- FREE
- Sept 7 – 10AM: 250th Labor Day Celebration at Rolling Acres Farm- $
- Sept 7 – 11AM: Labor Day Luau at MWR Dahlgren- FREE
- Sept 8 – 10AM: Fall Toddler Day at Rolling Acres Farm – $
- Sept 12 – 10AM- Indigenous Heritage Day at St. Mary’s City – FREE
- Sept 12 – 12PM: Annual Hunter’s Fun Bash at Calvert County Fairgrounds- $
- Sept 12 – 11AM: Community Resource Day at Victory Ministry International – FREE
- Sept 13 10AM: Super Hero Sunday at Ward Farm Park – $
- Sept 13 – 11AM: The Fan Zone at Bensville Park in White Plains- FREE
- Sept 13 – 3PM: Open House at Freedom Hill Horse Rescue- FREE
- Sept 16 – 7PM: Moonlight Maze at Rolling Acres Farm- $
- Sept. 17-20 – All Day: Charles County Fair in La Plata, MD – $
- Sept 19 – Dusk: Movie on The Beach at North Beach – FREE
- Sept. 19-20 – 10AM: Art Fest @ Annmarie Gardens- $
- Sept 20 – 12PM: Community Day at National Harbor- FREE
- Sept 24-27 – ALL DAY: St. Mary’s County Fair in Leonardtown, MD – $
- Sept 25 – 5PM: Cars, Cows and Classics at Chick-fil-a La Plata- FREE
- Sept 26 – 10AM: Pirate Day at Calvert Marine Museum – $
- Sept 26 – 11AM-4PM: River Fest at St. Mary’s City- FREE
- Sept 26 – 1PM: Harvest Festival at My Mustard Seed Refuge – $
- Sept 27 – 9AM-12PM: Car Show at Newburg VFD- FREE
- Sept. 30 – Oct 4 – All Day: Calvert County Fair in Prince Frederick, MD – $
- Oct 2-16- All Day: Scare Crow Stroll at Leonardtown Square- FREE
- Oct 3 – 10AM-4PM: Fall Harvest at Zekiah Farms- $
- Oct 3 – 10AM: Fall Craft Fair at Billingsley Com Center- FREE
- Oct 3- 10AM-2PM: Fall Fun Festival at Little Flowers School in Great Mills- $5
- Oct 3 – 11AM: Annual Solomons VFD Open House- FREE
- Oct 3- 12PM-5PM: 3RD ANNUAL FORT WASHINGTON FESTIVAL- FREE
- Oct 4 – 1PM-5PM: Fall Festival at La Plata Town Hall – FREE
- Oct 8 – 5PM: Daddy Daughter Date Night at Chick-fil-A in La Plata- $
- Oct 10 – 7AM-12PM: Fall Fishing Derby at Gilbert Run- $
- Oct 10- 10AM-4PM: MOAR’s Fall Festival in Saint Leonard- FREE
- Oct 10- 10AM-1PM: Family Fall Festival at Idlewilde Farms- $
- Oct 10- 11AM-3PM: Fall Community Festival at Victorious Kids in Indian Head- FREE
- Oct 10 – 12PM: Annual St. Leonard VFD Open House- FREE
- Oct 10 – 7PM: Moonlight Maze at Rolling Acres Farms- $
- Oct 10 – 12PM-4PM: Fire Prevention and Open House – FREE
- Oct 11, 18, 25- 12PM-4PM: Harvest Days at Serenity Farms- $
- Oct 11 – 12PM: Annual Apple Festival at Our Lady of the Wayside- FREE
- Oct 17 – 9:30AM: Village Days at Jefferson Patterson Park- FREE
- Oct 17- 10AM: Fall Festival & Colonial Faire at Maxwell Hall- FREE
- Oct 17- 10AM-1PM: Fall Festival at Indian Head MWF- FREE
- Oct 17 – 10AM-12PM: Fall Baby Bazaar at Somers – FREE
- Oct 17 – 11AM: Freedom Day at Lower Marlboro in Owings- FREE
- Oct 17- 12PM-2PM: Fall Festival at Grace Lutheran Church in La Plata- FREE
- Oct 18 – 12PM: Open House Huntington VFD- FREE
- Oct 22 – 4PM: Fall Harvest at MWR Dahlgren- FREE
- Oct 24 – 7PM: Moonlight Maze at Rolling Acres Farms- $
- Oct 24 – 10AM: Rosaryville Heritage & Trails Day in Upper Marlboro- FREE
- Oct 25 – 11AM: Community Fair at Kings Landing Park- FREE
- Oct 25 – 1PM-4PM: Fall Festival at Bensville Park- FREE
- Oct 31- 10AM-4PM: Harvest Fly In at Shannon’s Airport in Fredericksburg, VA- FREE
- Nov 6 – 5:30: Campfire On The Beach at North Beach- FREE
- Nov 7 – All Day: American Indian Heritage Day at Jefferson Patterson Park- FREE
- Nov 8 – 1PM: Salute to Veterans Parade at La Plata Town Hall- FREE
HALLOWEEN HAPPENINGS
- Sept. 19-Nov. 1- (Weekend Only-Day) Great Pumpkin Fest – Kings Dominion- $
- Sept. 18-Nov. 1 (Weekend Only-Night) Halloween Haunt – Kings Dominion- $
- Sept. 20-Oct. 2- (Day) Counts Spooktacular at Busch Gardens Williamsburg, VA- $
- Oct 2-25- 7PM: Addams Family at Newtowne Players in Lexington Park
- Oct 3- 7PM: Hotel Transylvania at My Gym Waldorf- $
- Oct 9- 5:30PM: Trunk or Treat and Movie Night at SJ Johnson – SOLD OUT
- Oct 10 – 7PM: Spooktacular Party at My Gym Waldorf- $
- Oct 10 – 11AM: Monster Market at Annmarie Gardens- $
- Oct 16- 4PM-8PM: Fall Fridays on the Farm Tractor Treat- $
- Oct 18- 5:30PM: Trunk or Treat at Sam’s Club in Waldorf-FREE
- Oct 21 – 5:30PM-7PM: Treats With The Trades at Calvert Career and Trade- FREE
- Oct 22 -5:30PM: Trunk or Treat at GKES in Great Mills- FREE
- Oct 22- 6PM-8PM: Trunk or Treat at La Plata Court House- FREE
- Oct 23- 6PM-8PM: Victorian Halloween at Dr. Mudd Museum- $
- Oct 23 – 6PM: Halloween at Hallowing Point Park in Prince Frederick- FREE
- Oct 23- 6PM-8PM: Trunk or Treat at Matula Elementary School – $
- Oct 24- 11AM: Sensory Friendly Trunk or Treat at Sparks in Waldorf- FREE
- Oct 24 – 11AM: Halloween in the Garden at Annmarie Gardens- $
- Oct 24 – 12PM: Trunk or Treat at Town Market in Waldorf- FREE
- Oct 24- 2PM-7PM: Spooky Fall Festival at the Shops at Waldorf- FREE
- Oct 24- 1PM-3PM: Trick-or-Treat Trail at Down Town La Plata- FREE
- Oct 24- 1PM: Monster Mash Bash at Leonardtown Wharf- FREE
- Oct 24- 2PM: Spooky Fall Festival at The Shops of Waldorf- FREE
- Oct 24 – 2PM-6PM: Spooky Fall Festival at Shops at Waldorf- FREE
- Oct 24- 3PM-6PM: Trunk or Treat at Sparkle and Sass – FREE
- Oct 24- 5PM-7PM: Trunk or Treat at SMYO Field in Pomfret- FREE
- Oct 24- 5PM-9PM: Trunk or Treat at Melwood- FREE
- Oct 24 – 5:30PM: Trunk or Treat at Mechanicsville VFD- FREE
- Oct 24 – 7PM: Spooktacular Party at My Gym Waldorf- $
- Oct 24 – 7PM: Guided Halloween Hike at American Chestnut Land Trust- FREE
- Oct 25 – 11AM: Tricks vs Treats Scrimmage Game at Charles County Fairgrounds- $
- Oct 25- 12PM-4PM: Trunk or Treat at St. Mary’s Animal Rescue- FREE
- Oct 25 – 1PM: Halloween With the Horse at Freedom Rescue- $
- Oct 25- 2PM-4PM: Trunk or Treat at Calvert County Fairgrounds- FREE
- Oct 25 – 3:30PM: Trunk or Treat at First Baptist Church in Waldorf- FREE
- Oct 25- 4PM-5:30: Halloween Trunk or Treat at Capital Clubhouse- FREE
- Oct 25 – 4PM: Trunk or Treat at Real Life Mechanicsville- FREE
- Oct 27-6PM-8PM: Trunk or Treat at All American Steakhouse – FREE
- Oct 27- 6PM-8PM- Trunk or Treat at B Funk in La Plata- FREE
- Oct 29 – 10AM: Halloween Pup Party – FREE
- Oct 29- 5PM-7PM: Trunk or Treat at Skyzone – FREE
- Oct 29 – 5:30PM: Spooky Story Trail at Pisgah Park- FREE
- Oct 30- 5:30PM: Trunk or Treat at Billingsley Elementary- FREE
- Oct 30- 5:30PM Trunk or Treat at Huntington VFD- FREE
- Oct 31- 9:30AM: Haunted Town at Imaginarium- $
- Oct 31 – 1PM-3PM: Trunk or Treat at Pax in Lexington Park – FREE
- Oct 31- 9AM-2PM: Halloween Harvest Bash at Duley Farm in Upper Marlboro- FREE
- Oct 31- 3PM-4PM: Trick or Trade! Pokemon Event at Root Bound Farms- FREE
- Oct 31- 4PM-10PM: Halloween Trunk or Treat at Serenity Farms- $
- Oct 31- 5PM-7PM: Trunk or Treat at Newburg RS&FD- FREE
- Oct 31 – 5PM: Trunk or Treat at Nanjemoy VFD- FREE
- Oct 31 – 6PM-8PM: Trunk or Treat at Village Green in Indian Head- FREE
- Oct 31- 6:30PM: Trunk or Treat at La Plata First Baptist- FREE
STORY TIME, CRAFTS & EDUCATIONAL
- Sept 4 – 1PM: First Friday Fossils at Calvert Marine Museum- $
- Sept 7 – 10AM: Make and Take: Dino Dig at Imaginarium – $
- Oct 10 – 2:30PM: Fairy Tale Ball at PD Brown Library – FREE
- Sept 12 – 11AM: Family Nature Walk at Annmarie Gardens- $
- Sept 13 – 10AM: Creature Feature at Calvert Marine Museum – $
- Sept 13 – 11AM: Family Clay Day at Annmarie Gardens- $
- Sept 16-17 – 9AM: Homeschool Day at Mt. Vernon- FREE
- Sept 18-19 – All Day: Public Archeological Dig @ Jefferson Patterson- FREE
- Sept 19 – 6:30PM- Pirates Tales at Kings Landing Park- $
- Sept 23 – 10AM- Little Explorers at St. Mary’s City – $
- Sept 25 – 2PM: Autumn Afternoon Tea Party at Waldorf West Library – FREE
- Sept 26 – 9AM- Archeological Dig at St. Mary’s City – $
- Sept 26- 11AM-2PM- Pumpkin Painting at Chick-fil-A Brandywine- FREE
- Oct 2 – 10AM: All About Snakes at North Beach – FREE
- Oct 2 – 1PM: First Fossil Friday at Calvert Marine Museum- $
- Oct 3 – 10AM- Walktober Hike at Flags Pond Park – $
- Oct 7 – 10AM: Little Explorers at St. Mary’s City- $
- Oct 10 – 6:30PM: Going Batty Campfire at Kings Landing Park – $
- Oct 17 – 9:30AM: Story Time In The Park at Port of Leonardtown Park – FREE
- Oct 17 – 10AM: Autumn Adventures at American Chestnut Society- FREE
- Oct 17 – 10AM: Chomp Saw Costume Create at Lexington Park Library – FREE
- Oct 19 – 6PM: Spooky Story Night at Leonardtown Library – FREE
- Oct 21 – 10AM: Little Explorers at St. Mary’s City- $
- Oct 22- 10AM: All About Owls at Battle Creek Cypress Swamp – $
- Oct 24 – All Day: Halloween at the library in Leonardtown- FREE
- Oct 28 – 6PM: Spooky Story Time at Lexington Park Library – FREE
- Oct 29- 6PM: Spooktacular at Lexington Park Library – FREE
- Oct 30 – 8PM- Star Party at Kings Landing Park – $
- Oct 31 – 10AM: Creepy Critters at North Beach Nature Center- FREE
- Oct 31 – 10AM: Trails and Tales at Gatewood Preserve- $
- Oct 31 – 1:30PM: Spooktacular Drop-in Craft at Charlotte Hall library – FREE
- Oct 31 – 2PM: Halloween Movie Night at Twin Beach Library – FREE
- Nov 14 – 10AM: Fall Colors at North Beach Nature Center – FREE
CREEPY CRAWLY CRAFTS TO DO AT HOME
- Go all out and decorate the house from the inside out!
- Host a glow in the dark Halloween Hunt
- Have a Halloween Scavenger Hunt
- Play a Halloween Game
- Sit back a relax with a Halloween Movie Marathon
- Host a neighborhood costume Bicycle Parade
- Create a creepy craft
- Experiment with eerie science
- Bake some spooky sweets
- Check out these creative and fun Halloween themed crafts- LINK.
***This annual Halloween Happenings Guide was created to help families plan their fall fun! This article took a lot of time and dedication to create. All information is intellectual property of The Playful Parent. Be sure to share this article with friends and follow The Playful Parent on social media.
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