Annapolis Fall Fun Guide 2023 - Anne Arundel Moms

It’s October and it’s officially Fall, y’all! This is the best time of the year for festivals, corn mazes, haunted houses and pumpkin patches! Scroll down for a list of all the fun Fall activities to enjoy with your family this season. 

Check back often as I’ll be adding events throughout the month. 

*Please note – While we make every effort to crosscheck links and event details, we always encourage you to do the same before making final plans. If details are missing or incorrect, please let us know so that we can correct them. Thanks for your help!

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Greenstreet Gardens Fall Festival

Open Weekends October 1-28 | 10:30am-5pm

Open Select Weekdays October 9 & 20th | 1-5pm

Get lost in our five-acre corn maze, take a trip around the farm on a hayride, and explore our pumpkin patch! Grab some animal treats and feed the animals, get your face and hair painted, and go ride around on the cow train! Other activities include our tire tower, corn pit, jumping pillow, woodlands, and so much more.

 Halloween Happening Haunted Barn & Hayride

Due to the impending weather, opening weekend has been postponed until Friday, October 20th. Open Fridays, Saturdays and Sundays October 20-29 | 7-10pm

Anne Arundel County Fairgrounds. More information coming!

Homestead Gardens’ Fall Festival

Open Weekends September 30-October 22 | 10am-4pm

Davidsonville location ONLY

Give your family the same enchanting experiences you had as a child; seeing the barnyard animals, taking hay rides, picking out pumpkins and connecting with the community. Create new traditions and make unforgettable family memories.

Knightongale Farm Fall Festival

Open Weekends September 30-October 29 | 10am-5pm

Pumpkin picking at Knightongale Farm has become a long-standing tradition for many families and friends. When kids come to our farm…they never want to leave because there is so much to do and see!  Because we are only open seasonally for 5 weeks a year, we make sure to pack the fun and activities for the kids!  In addition to the pumpkin patch and corn maze…we offer face painting, peddle tractors to ride, hay rides, pony rides, petting animals, food, drinks, and so much more!




Light House Pumpkin Patch

Open every day in October until we sell out! Weekend Hours ~ 10:00 am – 6:00 pm and Weekday Hours ~ 2:00 pm – 6:00 pm

Each October, the Friends of The Light House teams up with many volunteers from local churches to host our fun Pumpkin Patch at St. Martin’s Lutheran Church on Spa Road. Everyone has a great time! Come find your perfect pumpkin and support our beloved Light House at the same time. We feel very lucky to get our beautiful, local pumpkins through Farmer Johns of Kent Island, Maryland.  We are proud to support this local vendor, a St. Mary’s parishioner, and we have a smaller carbon footprint by buying local.  The pumpkins are super fresh and handpicked.  Farmer Johns graciously supplies us with a stunning variety of fantastic pumpkins at cost, helping us raise even more funds for The Light House!

MD Corn Maze

Open Weekends October 1-November 5 | 10am-7pm

There are so many fun activities included with your ticket: Hay Pyramid, Corn Pits, Jump-Pad, Feed the Animals, Ziplines, Tight Ropes, Pedal Tractors, Broom Swings, Tractors, Petting Zoo, Hayrides, Bubbles, Slingshots and an 8-Acre Corn Maze. Pony rides are an extra fee. Come hungry to enjoy the food trucks, vendors and visit the general store to go shopping! 



Maryland Renaissance Festival

Open Weekends October 1-22 | 10am-7pm

The 27 acre Village of Revel Grove comes to life each autumn with more than 200 professional performers on ten stages, a 3,000 seat arena with armored jousting on magnificent steeds and streets filled with village characters.  Join His Most Royal Highness King Henry VIII in the forests and glades with over 140 artisans exhibiting crafts in their own renaissance shops, five taverns featuring cool libations, 42 food and beverage emporiums providing a vast array of succulent and sweet treats to sate even the most hearty of appetites.

Montpelier Farm Fall Festival

Open Weekends September 16-November 5

OCTOBER: Weekend Fall Festival | Fridays 5-11pm, Saturdays 10am-11pm & Sundays 10am-7pm 

Weekday Playdays | Tuesday thru Thursday | 10am-3pm

From Pumpkin Picking and Hayrides, to our massive 7-Acre interactive Corn Maze.  There are so many activities for the entire family to enjoy!

Outdoor Movie Night at GameOn bar+arcade Annapolis

Every Sunday Night in October | 8pm 

Join us for an outdoor movie night every Sunday night in October starting at 8pm!

October 8th: Barbie

October 15th: Edward Scissorhands

October 22nd: Beetlejuice

October 29th: Halloween


West Street 2nd Annual Scarecrow Stroll

October 20-November 1

Halloween fun on West Street! From October 21st – 31st, scarecrows created by families, organizations, and businesses will line West Street from Church Circle to Westgate Circle. Prizes will be awarded to the top scarecrows in each category. Voting will begin October 21st. Join us for our Fall Fest on West on October 21st. Register now for Scarecrow Stroll at

Y Worry Farm Festival

Open Weekends October 1-28 | 10am-6pm

Y Worry Farm is a family-owned farm in Davidsonville that has been around for 33 years! Grab a wagon and wander through their 5-acre pumpkin patch for the perfect jack-o-lantern, or let the kids play in the corn stalk tee pee, hay bale pyramid, or their small corn maze. Check out their winter squash, gourds, straw, hay bales, and more- perfect for your Halloween and Fall decorating needs.


The Great Annapolis Coffee Crawl


Calling all coffee-crazed Annapolitans! Join the highly anticipated caffeine-fueled adventure of the fall…The Great Annapolis Coffee Crawl! Traverse through 11 of Annapolis’ finest independent coffee shops, getting a punch on your card with each delectable autumn drink. The race is on and the first 25 coffee aficionados to complete the crawl will score an exclusive prize.


Special Historic Hauntings

Thursdays, Fridays & Saturdays in October

During the month of October, we’re partnering with Historic Annapolis to offer Special Historic Hauntings. Our spirited guide will lead you through the dark alleys, spooky side streets, and lesser-known haunted sites of the old and creaky town of Annapolis. Hear from real diary entries and newspaper articles of what frightened early 18th-century folks. Also included is a stop inside historic Hogshead, where you will be immersed in the tales of those living in Annapolis during the Revolutionary War. Listen to stories of spirits that linger in the mist, and explore one of Annapolis’ best-known cemeteries. Special Historic Hauntings takes you back to a time of superstition and legend. And who knows, after a trip inside Hogshead, your own story may be added to the history of Annapolis!


Anne Arundel County Fairgrounds Flea Market and Tractor Pull

OCTOBER 7th | 8am-2pm

There will be tons of vendors filled with items for sale – old and new!


Halloween Costume Exchange at Wimsey Cove Framing and Fine Art Printing

OCTOBER 7th & 14th | 10:30am-1:30pm

It’s that time of year when the littles start deciding what they want to be for Halloween. But what do you do with their old costumes? What do you do if you don’t want to buy brand new costumes? This year, Macaroni KID Annapolis and Wimsey Cove Framing and Fine Art Printing are hosting a Halloween Costume Exchange. Bring your gently worn but ready-to-wear halloween costumes, dance or theater costumes, and accessories. Others will do the same. Then pick out what you want and take it home. It’s FREE! If you make your own costumes, this will be a great place to get fabric and accessories.


Storytime: Spooktacular Extravaganza at Park Books

OCTOBER 8th | 11am-1pm

Three wonderful local children’s authors will come and read their creep-tacular stories followed by a craft for each. Costumes or dress-up are always encouraged! Tickets are $10 per child. 


Bedtime Book Buddies for a “Not So Scary Costume Night” at Paws at the Mall

OCTOBER 12th | 6-7pm

The animals can’t wait to see your costumes and listen to your stories! This program is for readers 5-10 years old at Paws at the Mall, Annapolis Westfield Mall. Please register through the link below and refrain from bringing younger friends and siblings. Sign up here.


Very Superstitious: Friday the 13th at the Paca House

OCTOBER 13th | 5pm

Hear how people tried to guide their fate and protect their hearth and home from dangers, both seen and unseen. View a special collection item as you discover the hidden history of the past. Then, enjoy seasonal treats at the conclusion of the program.


Children’s Theatre of Annapolis Halloween Extravaganza

OCTOBER 13th | 5:30-9:30pm

COSTUMES – LOCAL VENDORS  – A HAUNTED HOUSE – MUSIC – FACE PAINTING – And more! BYOLC: Bring Your Own Lawn Chair for some of our outdoor events too! Buy tickets. 


St. Anne’s Cemetery Tour

OCTOBER 14th | 11am-12pm

Many former residents and people associated with the Hammond-Harwood House are buried at St. Anne’s Cemetery. On this tour visitors will discover the fascinating lives of the men and women who called Hammond-Harwood House home. Stories of husbands and wives with their descendants; children lost through childbirth, accidents or war; politicians, military heroes, and artisans are discussed in this 60-minute tour in this historic burial ground.


Halloween Costume Swap at Discoveries Library

OCTOBER 14th | 2-4pm

Tired of Halloween costumes that your child only wears for a few hours? Join us for the Second Annual Discoveries Halloween Costume Swap! You do not need to donate a costume to participate, however individuals must be present to select a costume. If you have a costume you would like to donate, we will be accepting clean, gently used costumes starting September 1.


Fall Fest at Annapolis Town Center

OCTOBER 15th | 12-3pm

Enjoy all things Fall: Pick your Own Pumpkin Patch and Painting, Hay Maze, Games and Crafts, Plant a Pansy in a Pumpkin, DIY S’mores, Face Painting, Costume Contest, Live Music, Food Trucks and Vintage Views Mobile Bar. The first 600 kids will receive a free gift with a donation of canned goods to the Anne Arundel County Food Bank! All quantities are limited and on a first come, first service basis. This event is free to the public and (light) rain or shine! Sponsored by Greenstreet Gardens.


Weems Creek Church HARVEST FEST

OCTOBER 15th | 3-5pm

Games, bounce house, crafts, chili cook off, petting zoo, food and more! FREE and all ages invited!


Dinner and a Classic Movie Night at Reynolds Tavern

OCTOBER 15th | 8:15pm

Every Sunday Night our Beer Garden becomes your Neighborhood Dinner and a Classic place. Kitchen Open until 10PM and full bar service throughout the evening.


Harvest Festival at Parley Room

OCTOBER 19th | 4-10pm

Fall Family Fun at Parley Room – Open to All! Pumpkin Giveaway, S’mores from Bake Believe Bakery, Hot Cocoa , Warm Apple Cider, Caramel Apples, Buck ‘a Shuck Oysters, Dance Party afterwards from 7-10pm with DJ DEEZY!


Dodgebo-ween Spooktacular – Costumes, Candy and DodgeBow

OCTOBER 20th | 6-8pm

Are you looking for a fun, safe, and unforgettable Halloween experience for the whole family? Look no further! Join us for Dodgebo-ween, a spooktacular evening filled with DodgeBow, costumes, candy, and more! Get ready to don your favorite costumes and indulge in a night of DodgeBow excitement! DodgeBow is an exhilarating combination of archery and dodgeball using Soft-Tipped arrows. It’s a game that’s easy to learn and fun for ages 7+. We’ll provide all the equipment and safety gear—you just bring the energy and your costume!


Blue Crab Cupcakes Trunk or Treat

OCTOBER 20th | 6-9pm

We’re SO excited because this year it will be even BIGGER and BETTER than last year! SO many trunks, more food trucks, more prizes, costume contests and still confirming a Kid’s Band to play! This event is open to the public and is so much fun for the whole family! If you are wanting to do a Trunk this year, please email us at [email protected] so we can send you a sign up link!


Rising Stars: Thriller Karaoke Night at Maryland Hall

OCTOBER 20th | 6-8pm

Riding high on the spectacular reception from our previous Karaoke Night, we’re thrilled to usher in a spooky twist! Introducing our Thriller Karaoke – (Costume) Night, a fusion of networking, artistic expression, and Halloween festivities.


Haunted Harbour Day at Annapolis Harbour Center

OCTOBER 21st | 10am-12:30pm

Throw on your most spellbinding costume for a day of Halloween magic! This interactive experience is filled with thrilling activities and spooky giveaways. THIS FREE, FAMILY-FRIENDLY HALLOWEEN EVENT INCLUDES: Trick-Or-Treating, Free Trick-Or-Treat Bag, Photo Scavenger Hunt, Children’s Costume Contest, Free Popcorn, Prizes & More, Balloon Artist, Magician, Fortune Teller & More!


Fall Harvest Day at Willow Oak Flower & Herb Farm

OCTOBER 21st | 10am-5:30pm

Enjoy the bounty of the season! Pick a pumpkin from our patch, paint a pumpkin $6, make a dried flower pumpkin $8, make a fall planter $20 and enjoy the season. Live music, children’s activities & food. $5 adult admission.


Spooktacular Storytime at Severna Park Library

OCTOBER 21st | 11am

Come in costume to enjoy not-so-scary stories, songs, and activities, followed by our traditional parade through the library!


Shoptoberfest at Severna Park Racquetball & Fitness Club

OCTOBER 21st | 11am-3pm

Don’t miss this fun, FREE, family event! We will have music, shopping, Trick or Treating, a costume contest, a photo booth and more!


Fall Fest on West

OCTOBER 21st | 2-9pm

Enjoy live music, pumpkins, kids’ events, outdoor dining and more on West Street in Historic Annapolis followed up with Dinner Under the Stars 5-9pm with live music. West St will be lined with Scarecrows and music from Church Circle to Westgate Circle – vote for your favorite! Register your scarecrow at


11th Annual Critter Crawl at Homestead Gardens

OCTOBER 21st | 2-3pm

Join us for the 11th Annual Homestead Gardens Critter Crawl! It’s a fantastic chance to showcase your pet’s Halloween spirit, compete for incredible prizes, and support our local SPCA of AA County. Sign up now until October 20th at midnight by completing the form provided at the bottom of this page. Don’t miss out on this amazing opportunity!


Fall Festival on Maryland Ave

OCTOBER 22nd |10am-5pm

October is knocking on the door… and that means our annual day of festivaling is just around the corner! We can’t wait to see you.


Kinder Farm Park Pop Up Harvest Festival

OCTOBER 22nd | 12-3pm

Hayrides. Pumpkin Painting. Kids Crafts. Face Painting. Meet the Animals. Photo Booth. CASH ONLY EVENT.


Dinner and a Classic Movie Night at Reynolds Tavern

OCTOBER 22nd | 8:15pm

Every Sunday Night our Beer Garden becomes your Neighborhood Dinner and a Classic place. Kitchen Open until 10PM and full bar service throughout the evening.


Spooky Storytime with Busch Library on the Green

OCTOBER 26th | 9:30am

Bring a blanket and join us for a spooktacular celebration of the season! Busch Library invites you and your little ones to an enchanting Storytime on the Green. It will be an educational and fun experience with crafts, free books, and giveaways! Costumes Encouraged! Reading level: Preschool ages 0-5. FREE EVENT!


Wassup Witches Spooky Good Time on Maryland Avenue

OCTOBER 26th | 5-8pm

We have got the whole of the Avenue in on the spooky good times this year! With lots of treats and no tricks in store for you.


Annapolis Bike Party Halloween Ride

OCTOBER 26th | 7:30pm | Acton Cove Annapolis

7:30 Meet up. 7:45 Wheels up.


Halloween Dance Party at Discoveries Library

OCTOBER 27th | 10:30am

Jump up, turn around, clap your hands and stomp around at this high energy Halloween bash. Costumes encouraged!


Witchy Walk at Quiet Waters Park

OCTOBER 27th | 5pm

Come in costume for a spooky witchy walk in the woods at Quiet Waters Park! Wear a witch hat, dress in your costume, and bring a friend! All ages welcome – bring the kiddos!  There may even be a special treat or maybe tricks too. Questions? Email [email protected] or [email protected]


USNA Annual Halloween / All Saints Concert

OCTOBER 27th | 7pm & 10pm and OCTOBER 28th | 7pm

A wide variety of music from multiple genres, including the famous Toccata and Fugue in D Minor, are featured in this concert celebrating the triumph of good over evil and All Saints’ Day. The incredible performances, special effects, and grand finale will leave you on the edge of your seat!


Hammond-Harwood House Pumpkin Walk

OCTOBER 27th | 4pm

Join us for our annual Pumpkin Walk! Come celebrate the spooky season with games, crafts, snacks, storytelling, face painting, and a costume parade around the mansion.


Annapolis Night Market 

OCTOBER 27th | 4-9pm | Ground Level of Hillman Parking Garage

Tis the Friday before Halloween and all the Great Annapolis Pumpkins have just been carved into jack-o-lanterns. The ground floor of the new Hillman Garage has been converted into a night market. Think of it as a part farmers market, part vintage market, and part art market. The one thing for sure is with live entertainment, great shopping, plenty of parking right above, and being a pre-Halloween weekend, it’s a good night to take a stroll to the new parking garage and in downtown Annapolis.


Halloween Spooktacular at the Severna Park Community Center

OCTOBER 27th | 5-8pm

FREE Family-Friendly event at the Severna Park Community Center. Join us for an evening fun for everyone in the family!


Halloween Bash in support of Annapolis Hope at Prism Annapolis

OCTOBER 27th | 9pm-12am

Music by DJ Lampdawg, costume contests, raffles and more!


Capital SUP Community Halloween Paddle 

OCTOBER 28th | 9:30-11am

Wear your best costume and meet us at Amos Garrett Park in Annapolis to paddle on Spa Creek to Ego Alley. A portion of proceeds will be going toward @livewaterfoundation


Room on the Broom Storytime and Scavenger Hunt at Eastport Library

OCTOBER 28th | 10am

Join us for a storytime and scavenger hunt based on the book Room On the Broom. Costumes are welcome!


FREE Trunk-o’-Treat Festival at Pip Moyer Recreation Center

OCTOBER 28th | 10am-2pm

Join us for a Spooktacular celebration of all things Halloween at our Trunk-o’-Treat Festival! Activities like this have a rich history of bringing neighbors and families together for a day of festive fun. Trunk-o’-Treat originated as a safer alternative to traditional trick-or-treating, providing a secure and enjoyable environment for kids to collect candies and enjoy Halloween-themed activities. We’ll gather at the Pip Moyer Recreation Center parking lot, where you’ll find a thrilling array of entertainment. There’s something for everyone, from games to hayrides to arts and crafts, that will ignite your creativity. Plus, we encourage parents to get in on the fun by decorating their cars in spooky or whimsical themes – the more creative, the better! Don’t miss out on the delicious food (and candy!) and the chance to mingle with friends and neighbors as we celebrate this cherished holiday tradition. Come one, all, and make this year’s Trunk-o’-Treat an unforgettable Halloween experience! We can’t wait to see you there!


Spook-Tackular Storytime and Costume Parade at Broadneck Library

OCTOBER 28th | 11am

Don your Halloween costume and come join us at the Broadneck Library for a Halloween themed storytime and party! We’ll be celebrating the spooky season with some silly Halloween stories, a costume parade, and more treats & activities!


SPCA’s Trick or Treat Trail

OCTOBER 28th & OCTOBER 29th | 12-5pm

We will be turning our Nature Trail, on the SPCA grounds, into a fun Halloween trail, appropriate for all ages!  Families are invited to come, dress up, and bring your dogs along for a themed Halloween experience through the woods. Costumes are encouraged.   No scary frights, only fun & spooky Halloween festivities! There will be Halloween decorations and creepy scenes along the outdoor trail, but nothing will jump up or pop-out at you or your pets.


City of Annapolis: Day of the Dead Festival at Maryland Hall

OCTOBER 28th | 3-8pm

Come enjoy Latin American food and drinks, live performances, Latino art/handcrafts gallery, sugar skill “skeleton” face painting, mask making, kids zone, altar of the dead, Latino art gallery and more!


Whispers of the Raven: An Edgar Allan Poe-Inspired Evening of Eerie Echoes

OCTOBER 28th | 7-8:30pm at the Hammond-Harwood House

We invite you to join us for an unforgettable Halloween experience that celebrates the literary legacy of Edgar Allan Poe. Whispers of the Raven promises to captivate your senses, leaving you spellbound by the echoes of his words and the enchantment of the evening.


SPCA’s Forest of Fear Haunted Trail

OCTOBER 28th & OCTOBER 29th | 7:30-10pm

During the daytime, the SPCA is hosting a family & pet friendly Trick or Treat Trail. However, once the moon rises and the zombies start to creep out, our nature trail will transform into the FOREST OF FEAR – a Haunted Trail experience! Dare you trek through the wicked woods of the SPCA’s Nature Trail as it becomes home to wild werewolves and ghastly ghouls? This adventure through the dark is for brave souls only , as monsters WILL jump out and try to scare you. Do not bring your dog to this night-time haunted trail. Admission is $15 per person and must be purchased online. Each individual who wishes to experience the haunted trail must have their own admission. All proceeds benefit the SPCA of Anne Arundel County and our homeless animals.


The Brick Companies’ Zombie Dash 5k, Kids Fun Run and Inflatable Costume Mad Dash

OCTOBER 29th | 10am at the Smithsonian Environmental Research Center (SERC)

Get ready for a fun-filled day perfect for the entire family featuring: Fun and scenic 5k run course with lots of hidden zombies, Kids Fun Run, Inflatable Costume Mad Dash, Finish-line medals for all participants, Participant shirts for all registered 5k participants, Skele-bration Zone with lots of tricks and treats, including local food and beverage vendors. 5k entry includes one complimentary beer or non-alcoholic beverage.


BOO BASH at Goldfish Swim School Waugh Chapel

OCTOBER 29th | 12-2pm

Join us for a FREE Halloween-themed splashing fun time! Trick-or-Treat in our Changing Huts 12-12:30pm. Enjoy lobby games from start to finish from 12-2pm. SWIM together as a family from 12:45-1:45pm!  Call to reserve your space in the Splashy Scary Festivities! (410) 413-7065. Arriving in your Halloween Costume is welcome and encouraged!


Parley Room’s Pumpkin Carving Party

OCTOBER 29th | 12-3pm

Parley Room is providing the pumpkins and the carving kits, we just need you! Join us for a good old fashioned pumpkin carving party! The best pumpkin wins $100 gift card to Parley Room or $100 Amazon gift card! Spots are limited so call 443-837-6481 to reserve yours!


Wordsmith Poetry “Haunted Verses” at 49 West Coffeehouse

OCTOBER 29th | 4-6pm

Local poets gather to deliver some haunted tales.


Dinner and a Classic Movie Night at Reynolds Tavern

OCTOBER 29th | 8:15pm

Every Sunday Night our Beer Garden becomes your Neighborhood Dinner and a Classic place. Kitchen Open until 10PM and full bar service throughout the evening.


Mr. Paca’s Garden Storytime: Halloween is Coming

OCTOBER 31st | 10am

Get ready, ghosts, goblins, witches, and monsters, Halloween is here! Halloween is Coming brings back memories of neighborhood trick or treating, the joy of a homemade costume, and the sounds of things that go bump in the night. Join us for our annual pumpkin find in our beautiful 18th century garden! Don’t forget to wear your favorite Halloween costume! 


Trick or Treat at Westfield Annapolis Mall

OCTOBER 31st | 4-7pm

Trick or Treat in a safe, dry environment at Westfield Annapolis. Start at the library to decorate a treat bag, then visit other retailers for some treats!


Arundel Volunteer Fire Department Station 7 Terror Trail

Open Weekends September 30-October 28 | 7:30-10pm

A family friendly haunt with activities for everyone. We have a scary Terror trail recommended for 8 years and older and offer activities for younger children at the ticket booth and families can enjoy our Boo Haunt loop – geared for those under 8 years old. We are supporting the Arundel Volunteer Fire Department. All proceeds from the Haunted Trail.


No So Spooky Haunted Hayride and Haunted Orchard Walk at Hansel Hill Farm

Open Weekends October 6-30 | Varying times from 4-9pm

Our “Not so Spooky Hayride” is great for all ages and includes a trip around the farm to look at our fun Halloween Inflatables.  Explore the farm once you’re done and find our hidden candy spots. Our “Haunted Orchard Walk” is geared towards older kids and adults, however, a few braver little ones have survived.  Daytime visits are less scary than when it’s dark. Each ticket includes admission to both adventures.  Kids 2 and under are free. Tickets are $10 each if ordered in advance, and $15 each at the door.

What’s your family’s favorite Fall activity? 


We’ll be updating this list over the next couple of weeks so check back for updates! If we’re missing your favorite Fall activity, email it to us at [email protected].


Have fun!!

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