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Halloween / Fall Activities

Alright Mamas..... here is a list of kid friendly Halloween & fall activities in or near Winchester

Please check with the events linked website pages for more information, hours, and pricing!

Also, check back to WinchesterMoms Calendar of Events page for any updated Halloween events!


Trunk OR Treat & Children's Costume Contest hosted by WinchesterMoms and 0-60 Energy Cafe

When? October 29

Time? 1-3pm

Where? 0-60 Energy Cafe located at 170 Delco Plaza, Winchester, VA 22602

Tell me more! ​0-60 Energy Cafe & WinchesterMoms are teaming up for this fun Trunk OR Treat & Children's Costume Contest event! Children's costume contest with prizes will start at 1:30 pm and Trunk Or Treating will be ongoing from 1-3 pm. There will be some fun, sporty, and even exotic cars lined up with their trunks full of candy for your little ones! This event is free and will be lots of fun! so come on out with your little ones! ***Children that are interested in being apart of the costume contest, email winchestermoms@gmail.com to get your little ones signed up! It's free!

Spooktacular in Old Town

When? October 28

Time? 2-4pm

Where? Loudoun Street Walking Mall in Old Town Winchester

Tell me more! The annual Spooktacular returns to the Loudoun Street Mall with loads of fun for the whole family. Businesses along the mall participate in this popular free community event by handing out candy or small trinkets.

The festivities begin with a pet costume parade at 11 a.m. organized by Posh Pets Boutique. The trick-or-treating begins at 2 p.m. and wraps up at 4 p.m.

What's New Worship Trunk or Treat

When? October 29

Time? 2 PM - 5 PM

Where? What's New Worship located at 2249 Valor Dr, Winchester, Virginia 22601

Tell me more! Enjoy an afternoon of fun fall events!

Halloween Boo Bash

When? October 30

Time? 5:30 pm

Where? Apple Blossom Mall located at 1850 Apple Blossom Dr, Winchester, Virginia 22601

Tell me more! Kids will parade around mall storefronts for treats given out by our retailers. Your children can also compete in the annual Halloween Costume Contest. Kids up to age 12.

Trunk or Treat & Car Show

When? October 14

Time? 4-8 pm

Where? Dowell J. Howard Center located at 156 Dowell J Circle, Winchester VA

Tell me more! This is an evening of costumes, candy and cars!

Halloween Trunk & Treat & Costume Contest Family Drive In

When? October 21 & 28

Time? Oct. 21- 4-7 pm / Oct. 28- 5-7 pm

Where? Family Drive-In Theater located at 5890 Valley Pike, Stephens City, Virginia 22655

Tell me more! It's their annual Halloween Trunk or Treat & Costume Party- now held on two Saturdays in October- the 21st and 28th! Bring the kids out dressed in costumes, and have them Trunk or Treat before the movie. Costume contests for all age groups- children, teens, adults, & pets. Halloween related movies for families on screen 1 and more horror style films on screen 2 for adults & teens.

Spooktacular Halloween

When? October 28

Time? 3-5 pm

Where? Rutherford Crossing located at 151 Market St, Winchester, Virginia 22603

Tell me more! Participating stores will have a sign in their storefront window. Costumes are encouraged.


The Pumpkin Patch at Hill High Farm

Admission and parking is always free, and there are many free activities to enjoy on the farm such as a petting zoo, a round bale maze and a pirate ship jungle gym. There are also additional activities that require a fee, which include a wagon ride out to the pumpkin patch where you can pick your own pumpkin, a three mile path corn maze, and a family friendly moonlit hayride out to the pumpkin patch to pick your own pumpkin!

Hill High Farm is located locally in Winchester Va!

Wayside Farm

This year's maze theme is Pokemon...come see if you can wind your way through their 10-acre maze. This farm also offers pig races on festival days, huge pumpkin patch where you can pick your very own pumpkin right from the the vine, slides, kids play yard, farm animals, giant jumping pillow, and more!

Wayside Farm is located in Berryville, VA at 5273 Harry Byrd Highway Berryville, Virginia 22611

Great Country Farm

Great Country Farm offers lots to do including a Cow train, giant jumping pillow, farm animals, P-Rex the pumpkin munchin’ dinosaur, pig races, pick your own pumpkins at the pumpkin patch, and more! Great Country Farms is located at 18780 Foggy Bottom Road, Bluemont, VA 20135

West Oaks Farm Market

West Oaks Farm Market offers a 5 acre corn maze with over 2 miles of paths (a beginners and advanced maze) and a pick-your-own pumpkin in the Patch.

West Oaks Farm Market is located locally at 4305 Middle Rd Winchester, VA 22602.

Orr's Pumpkin Patch

Orr's Pumpkin Patch is located in Martinsburg, WV, just a short drive from Winchester up 81 North. Orr's pumpkin patch offers a hayride to the patch, pick your own pumpkin, small corn maze, and more. This pumpkin patch is also apart of the Orr's Farmer's Market, which has a bakery and other goods for sale. Check their schedule for live music as well!

Orr's pumpkin patch is located at 682 Orr Dr, Martinsburg, WV 25403.

Old McDonald's Pumpkin Patch & Corn Maze

Old McDonald's Pumpkin patch is a short drive to Inwood, WV and offers 5 acre corn maze, giant slides, corn castle, playground, corn hole, antique tractor display, and hayrides.

Old McDonald's is located at 1597 Arden Nollville Road Inwood, WV 25428

The Corn Maze In The Plains

This one is about a 45 minute drive from Winchester, but if you are looking to try something new, this place has been voted "the top corn maze attraction in the DC area"! It is also more than just a corn maze! The Corn Maze in the Plains also offers hay rides, farm animals, a pumpkin sling shots, giant slides, farm obstacle course and more!

The Corn Maze In The Plains is located at 4501 Old Tavern Rd. The Plains, Va 20198

Cox Farm

Cox Farm is just over an hour drive from Winchester, so this is another choice if you are looking for something new to try that's not in Winchester! Cox Farm is filled with activities for the whole family including hay rides, slides, animal farm, kiddie zone, rope swings, and more!

Cox Farm is located at 15621 Braddock Rd Centreville, VA 20120.


Pumpkin Festival at Marker Miller Orchards

Marker Miller's Pumpkin Festival is October 21 from 9 am - 5 pm in Winchester, VA.

Choose from ones already picked or pick your own. Enjoy pumpkin pie, pumpkin rolls, pumpkin bars and pumpkin donuts from our bakery. A variety of food will be available at the food building.

The GLOW: A Jack O’Lantern Experience

The GLOW is a family friendly event in Reston, VA, which is about an hour drive from Winchester.

This experience takes you on a 1/3 mile glowing trail pumpkin wonderland filled with over 5,000 hand carved jack o’ lanterns. The GLOW is appropriate for all ages, not scary, and stroller friendly! The GLOW runs from October 5-29. If you get a chance to go to the GLOW, they encourage you to use #theglowdc when you post your pictures!

Third Annual Boo at the Zoo

Boo at the Zoo is October 14 from 9am - 6pm at Wilson's Wild Animal Park in Winchester, VA.

The third Annual Boo at the Zoo offer several activities such as a petting area, wagon ride, pumpkin decorating, Slide, Corn pit, Face painting, and more!

Trick-or-Treat 5K & Family Fun Run

This event is held at the Sky Meadows State Park in Delaplne, VA October 22 from 2-5 pm. Runners, walkers and families are encouraged to wear costumes and do their best to conquer the course while completing all 5 fun-stations along the way. Then stick around to enjoy the Family Farm Days at the park!

Harvest Hoedown

This event is at the Hagerstown Fairgrounds in Hagerstown, MD on October 14 from 1-4 pm.

There will be balloon bending & sculpting, pony rides & petting zoo, pumpkin painting, face painting, barrel cart rides & hay rides, rock climbing wall, and more!


Winchester Spring Valley Farm Market

located at 2454 Northwestern Pike Winchester, Virginia

Virginia Farm Market

located at 1881 N Frederick Pike Winchester, Virginia 22603

Marker-Miller Orchards Farm Market

located at 3035 Cedar Creek Grade Winchester, Virginia 22602

The Homestead Farm at Fruit Hill Orchard

Located at 2502 N. Frederick Pike Winchester, Virginia 22603

Woodbine Farm Market

Located at 5199 John Marshall Hwy Strasburg, Virginia 22657

Realtor Chic is a VA licensed Realtor who specializes in Winchester and Northern Virginia. Check out her home decor blog! Looking to buy or sell? Contact Realtor Chic today!

Kid Friendly Halloween Books

The Spooky Wheels on the Bus

Count from One Spooky Bus up to Ten Goofy Ghosts as this Halloween ride races through town picking up a few unsuspecting passengers along the way.

Pete the Cat: Trick or Pete

Pete loves Halloween and candy but not so much scary surprises. Follow Pete as he goes trick-or-treating from house to house and discover what is waiting behind each door.

Goodnight Goon: A Petrifying Parody

This is my 4 year old's favorite Halloween book! We bought it last year for Halloween, and he still picks this book out to read for his bedtime story quite frequently!


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