I know I’m not alone in feeling like the summer swam by too quickly and autumn is arriving too fast. Believe it or not, many farms are opening this weekend, fall festivals are beginning, and even trunk or treating events are scheduled. To stay ahead of things…Here is a lengthy list that will continue to grow as October approaches. Please check back frequently, as this article will be updated regularly.
FALL FESTIVALS & COMMUNITY EVENTS
- Aug. 23-Oct.19, 2025 (Weekends) All Day – MD Renaissance Festival in Annapolis- $
- Aug. 30 10AM-6PM- Jousting Tournament @ Christ Church Port Republic- $
- Aug. 30 5PM-9PM- End of Season Bash @ Leonardtown Wharf- FREE
- Sept. 5 5PM-8PM- Art & Entertainment Celebration @Leonardtown Square- FREE
- Sept. 5-7- 10AM-3PM Sidewalk Art Contest in Leonardtown- FREE
- Sept. 5-7 10AM-4PM – Fall Festival Opening Weekend Rolling Acres Farms in Port Republic- $
- Sept. 5 7:30PM- Outdoor Movie Night @Dahlgren Parade Field- FREE
- Sept. 6 10AM-4PM- Indigenous Heritage Day in St. Mary’s City, MD- FREE
- Sept 6-7 10AM-3PM- Fall Fun on the Farm @ Kings Family Farm – $
- Sept. 7- 6PM- Youth & Family Night @ Real Life Mechanicsville- FREE
- Sept. 8 9AM-12AM- Fall Fest Toddler Days @ Rolling Acres Farm- $
- Sept. 10 10AM-12PM- Teddy Bear Picnic @Historic St. Mary’s- $
- Sept. 11-14- All Day- Charles County Fair in La Plata, MD – $
- Sept. 13 9AM-12PM- Meadows Matter: Nature Walk @Port Tobacco River Park-FREE
- Sept 13 3PM- Open House @ Freedom Hill Horse Rescue- FREE
- Sept. 13 7:30PM- Outdoor Movie Bettle Juice @North Beach – FREE
- Sept. 14-15- 10AM-4PM- Harvest Festival at Horsmon Farm in St Leonard, MD- $
- Sept. 17-18- All Day- Fall Homeschool Days @ Mt. Vernon- $
- Sept 18 10AM- Talk Like A Pirate Day @ CCPR Mt. Hope Comm Center – $
- Sept 18-21- All Day at the St. Mary’s County Fair in Leonardtown, MD – $
- Sept. 20 10AM- Art Fest @ Annmarie Gardens- $
- Sept. 20 10AM-3PM Pirate Day @ Calvert Marine Museum- $2
- Sept. 20- 11AM- Kids Pirate Cruise @ Calvert Maarine Museum- $
- Sept. 20- 10AM-3PM- Village Day @ Jefferson Patterson- FREE
- Sept. 22 10AM- Magic School Bus Event @ CCPR Mt. Hope – FREE
- Sept. 24-28 All Day- Calvert County Fair in Prince Frederick, MD – $
- Sept 26 7PM-9PM- Outdoor Movie @ Leonardtown Wharf- FREE
- Sept. 26- 7PM-10PM- Maze Craze in the Moon Light at Rolling Acres Farm- $
- Sept. 27- 11AM-4PM- River Fest in St. Mary’s City- FREE
- Sept. 27- 10AM-2PM- Monarchs & Milkweed at Merkle Wild Life in Upper Marlboro- FREE
- Oct. 3-30- All Day- Annual Scarecrow Stroll @Leonardtown Square- FREE
- Oct. 4-5- 10AM-5PM- Scarecrow Making @Horsmon Farm- $
- Oct. 5 12PM-1:30PM- Fall Family Day @ Northeast Community Center
- Oct. 5- 1PM-3PM- Annual Tractor Parade @ Leonardtown Square- FREE
- Oct. 6 7:30PM- Full Moon Hike @Battle Creek Cypress Swamp Sanctuary- FREE
- Oct. 7- 4PM- Bat Night Hike @Westlands Over Look Park- FREE
- Oct. 8 10AM-12PM- Little Explorers- Fall Colors @Historic St. Mary’s- $
- Oct. 10- 7PM-10PM- Maze Craze in the Moon Light at Rolling Acres Farm- $
- Oct. 11-12 10AM-5PM- Fairy Magic @Horsmon Farm- $
- Oct. 11- 10AM-4PM- Annual Fall Festival at Zekiah Farms in Waldorf, MD- FREE
- Oct. 12 12PM- Annual Apple Festival @Our Lady of the Wayside- FREE
- Oct. 18 & 19- 10AM-3PM- Colonial Faire and Fall Festival@ Maxwell Hall- FREE
- Oct. 18 10AM-3PM- Village Days @ Jefferson Patterson- FREE
- Oct. 18 4:30PM- Harvest Festival @Dahlgren Naval Base- FREE
- Oct. 24 4PM-6:30PM- Fall Festival @ Chick-fil-A Brandywine- FREE
- Oct. 24- 7PM-10PM- Maze Craze in the Moon Light at Rolling Acres Farm- $
- Oct. 26 10AM-5PM- Tractor Show @Horsmon Farm- $
- Oct. 26- 1PM-4PM- Fall Festival @ Bensville Park – FREE
- Oct. 310- 10:30AM-12:30PM- Fall Festival @Every Day Play n Learn – $3 Per Kid
- Oct. 31 6PM-8PM- Hallelujah Night Family Carnival- FREE
- Nov 1- 2PM-6PM- Fall Festivals @Bethel Baptist Church in La Plata- FREE
- Nov. 1-2- 10AM-5PM- Rage Against the Pumpkin @Horsmon Farm- $
- Nov. 9 1PM- Veteran’s Day Parade @ La Plata Town Hall- FREE
HALLOWEEN HAPPENINGS
- Sept. 13-Oct. 2 All Day- BOO Fest (Weekends-Day) at Six Flags America in Bowie- $
- Sept. 13-Oct. 2 All Day- Fright Fest (Weekends-Night) at Six Flags America in Bowie- $
- Sept. 20-Nov. 2- (Weekend Only-Day) Great Pumpkin Fest – Kings Dominion- $
- Sept. 20-Nov. 2 (Weekend Only-Night) Halloween Haunt – Kings Dominion- $
- Sept. 21-Oct. 3- (Day) Counts Spooktacular at Busch Gardens Williamsburg, VA- $
- Oct. 17- Nov. 1- (Friday-Saturday & Halloween)-7:30PM-10PM Vampire Manor- $
- Oct. 4 9AM- Monster Market @ Annmarie Gardens- FREE
- Oct. 4 6PM-9PM- Hotel Transylvania Party @ My Gym in Waldorf- $
- Oct. 5 12PM-3PM- Fall Festival @ La Plata Town Hall- FREE
- Oct. 6 6PM- Halloween Monster Mash Dance @CCPR Southern Center- $
- Oct. 10- 5:30PM-9PM- Trunk or Treat & Movie in Huntingtown, MD – FREE
- Oct. 11 10AM- Great Halloween Costume Exchange @CCPR Southern Center- FREE
- Oct. 17 6PM-8PM- Trunk or Treat @ Matula Elementary School – $2
- Oct. 17 7PM- Frightful Fun Halloween Celebreation @ CCPR Mt. Hope Center- FREE
- Oct. 18 2PM-6PM- Spooky Fall Fest @Shops at Waldorf Center- FREE
- Oct. 18 5PM-8PM- Lost City in Historic St. Mary’s City- $
- Oct. 18 6PM-10PM- Spooktacular Halloween Party Kids Night Out @ MyGym in Waldorf- $
- Oct. 18 10AM-4PM- Halloween in the Garden @Annmarie Garden- $
- Oct. 18 2PM- Annual Fall Festival @ The Shops at Waldorf- FREE
- Oct. 19 1PM-4PM- Monster Mash Bash – Leonardtown- FREE
- Oct. 22 10AM-12PM- Little Explorers: Halloween @ Historic St. Mary’s City- $
- Oct. 22 5:30PM – 7PM – Treats With The Trades @Calvert Career Tech Center- FREE
- Oct. 22 6PM-7PM- Trunk or Treat @ Morningside of House in Waldorf- FREE
- Oct. 23 5:30PM- Trunk or Treat @ William B Wade in Waldorf- FREE
- Oct. 24- 4:30PM- Trunk or Treat @Dental Care on Stanhaven in White Plains- FREE
- Oct. 24 4:30PM-5:30PM- Spooktacular Party @ My Gym in Waldorf- $
- Oct. 24 5PM-7PM- Trunk or Treat @Our Lady Star of the Sea- FREE
- Oct. 24 6PM-7:30PM- Trunk or Treat @Higdon in Newburg- $2
- Oct. 24 6PM-9PM – Halloween @ Hallowing Point Park – FREE
- Oct. 24 6:30PM- Trunk or Treat @ Inspired Day Learning Center- FREE
- Oct. 25 9AM-5PM- Trunk or Treat Vendor Show – Town Market in Leonardtown-FREE
- Oct. 25 10AM Haunted Town at Imaginarium
- Oct. 25- 5:30PM-8PM- Trunk or Treat at Mechanicsville VRS- FREE
- Oct. 25- 10AM-5PM Halloween Blaster Battle @ Charles County Fair Grounds- $
- Oct. 25 12PM-3PM- Trick or Treat Trail in Downtown La Plata- FREE
- Oct. 25 1PM-3PM- Trunk or Treat @ A Place to Grow in Waldorf- FREE
- Oct. 25 3PM- Boo Bash @ North Beach- FREE
- Oct. 25 5PM- Trunk or Treat & Movie Night @SMYO – FREE
- Oct. 25- 5PM-9PM- Fright Night Haunted Trail @North Point- $20
- Oct. 25- 7PM-8PM- Haunted House@ FCF in Waldorf- $
- Oct. 26 12:30PM-5PM- Harbor Halloween @ National Harbor- FREE
- Oct. 26 1PM-4PM- Trunk or Treat @ Bryans Road VFD- FREE
- Oct. 26- 3PM-6PM- RedRum vs Slashers Roller Derby Bout@ La Plata Fair Grounds- $
- Oct. 26 4PM-8PM Fall Festival at Real Life Church in Mechanicsville, MD – FREE
- Oct. 26 3:30PM- Trunk or Treat @First Baptist Church of Waldorf- FREE
- Oct. 26 6PM-7:30PM- Trunk or Treat @ La Plata HS Key Club- FREE
- Oct. 28 6PM-8PM- Trunk or Treat@ B-Funk in La Plata- FREE
- Oct. 28- 5:30PM- Trunk or Treat@ La Plata Church of Christ- FREE
- Oct. 28- 6PM-8PM- Trunk or Treat@ All American Steak House- FREE
- Oct. 29 5PM-7PM- Trunk or Treat@ Nanjemoy VFD- FREE
- Oct. 29 5:30PM-8PM- Little Ghouls and Goblins Bash @ Port Tobacco Restaurant- FREE
- Oct. 29 6PM-8PM- Trunk or Treat @ Westlake VFD in Waldorf- FREE
- Oct. 29 6PM-8PM- Trunk or Treat @Lackey HS- FREE
- Oct. 29 9:30AM- Halloween Bash @ CCPR Southern Com Center in Lusby- FREE
- Oct. 30 10AM- Halloween Puppy Parade @ Dunkirk Park – FREE
- Oct. 30 4:30PM- Trunk or Treat @Dahlgren MWR Jenkins Road- FREE
- Oct. 30 5PM-7PM- Trunk or Treat @Waldorf Ford- FREE
- Oct. 30 5PM-7PM- Trunk or Treat@ Waldorf Waldorf Toyota- FREE
- Oct. 30 5PM-7PM- Trunk or Treat @Stethem in Pomfret- FREE
- Oct. 30 6PM-8PM- Trunk or Treat @Charles County Sheriff’s – FREE
- Oct. 31 11AM- Creepy Creatures @North Beach Nature Center – FREE
- Oct. 31 5PM-7PM- Trunk or Treat @ RVFD Trunk or Treat in Ridge – FREE
- Oct. 31 5PM-9PM- Spooktacular @ Melwood – FREE
- Oct. 31- 6PM-8PM- Trunk or Treat at The Church of St. Charles- FREE
- Oct. 31 6PM-8PM- Trunk or Treat @ Village Green Pavilion in Indian Head- FREE
- Oct. 31 6PM-8PM- Trunk or Treat @ Southern Calvert Baptist in Lusby- FREE
- Oct. 31 6PM-8PM- Trunk or Treat @ Accokeek VFD- FREE
- Oct. 31 6:30PM Trunk or Treat @ First Baptist Church of La Plata – FREE
- Nov. 1 12PM-5PM- Trailer or Treat @ Safe Haven Stables in Charlotte Hall- $5
Nov. 1 5:30PM – 8PM- Trunk or Treat @Newburg VFD- FREE
STORY TIME & CRAFTS
Sept. 7 3PM- Storytime on the Farm @ Mrs. Moo’s in Prince Frederick- FREE
Sept. 19 6PM- Boo Buckets @Kids Art Skool in Prince Frederick- $
Sept 26 5PM- Halloween Nutcracker Craft @ Kids Art Skool in Prince Frederick- $
Oct. 1 6PM-7PM- Step into the Shadows: Unmasking Jack the Ripper @ Waldorf West Library- FREE
Oct. 8 2PM-3PM- Paint Your Own Mini Pumpkin @ CCLP PD Brown Branch- FREE
Oct. 9 2PM-3PM- History of Gourd Art @ CCPL Potomac Branch- FREE
Oct. 11 2PM-3PM- Pumpkin Palooza @ CCPL Potomac Branch- FREE
Oct. 16 6PM- Ghostly Glow Party @ CCPL Potomac Branch – FREE
Oct. 16 5:30PM- Franken Squish @ SCPL Lexington Park Branch- FREE
Oct. 17 3:30PM- STEM Fun Pumpkin Palooza @SCPL Charlotte Hall Branch- FREE
Oct. 18 2PM- Stain Glass Bat @ Calvert Boys and Girls Club- $
Oct. 21 5:30PM- Fall Suncatcher @ CCPL BD Brown – FREE
Oct. 22 3PM- Jekyll & Hyde Escape Room @ SCPL Leonardtown- FREE
Oct. 25 1PM-3PM- Movie & Pumkin Painting @ Classique Atelier- $40
Oct. 25 2:30PM- Make Your Own Potions @ SCPL Charlotte Hall- FREE
Oct. 30 6PM- Spooktacular Halloween Party @ SCPL Lexington Park – FREE
Oct. 30 6PM- Spooktacular Halloween Party @ SCPL Leonardtown- FREE
Oct. 31 2:30PM- Spooktacular Halloween Party @ SCPL Lexington Park – 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, if you like what you see consider donating to the Non-Profit on Patreon.***
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