First Night Winchester

First Night Winchester is a celebration of the arts, created by and for the community, as a safe and healthy way to usher in the New Year. The event takes place in historic downtown Winchester in a variety of venues.

Ring in the New Year with a full day of activities. We offer entertainment for nearly every age and taste: musicians, dancers, magicians, comedy, and so much more. Finish the day as we countdown the end of 2021 with our Apple Drop. And, welcome 2022 with a spectacular fireworks display at midnight!

All events will take place regardless of weather.

Purchase of First Night Winchester admission allows you access to:

New Year’s Eve events
Children’s Activities: 10am-5pm
6pm | 8pm | 10pm Performances
7pm | 9pm | 11pm Performances
8-11pm Musical Artists and Buskers
11pm Dance Party
Apple Countdown & Midnight Fireworks

The next day, on New Year’s Day at noon, there will also be a noon walk on the Trails at the Museum of the Shenandoah Valley.

At this time, all venues require you to wear a mask indoors, regardless of vaccination status.

Admission wristbands can be purchased online and picked up or purchased in person beginning December 21st and running through December 31st. For 10 days only, you can buy your admission for $10 per person, children 5 and under are FREE. You can purchase your wristband at the locations below.

Winchester-Frederick County Visitors Center on Pleasant Valley Road, open daily 9-5
Museum of the Shenandoah Valley – Gift Shop
Winchester Book Gallery

On December 31st, First Night Winchester Headquarters is located at 33 E. Boscawen Street. Only then can you purchase your wristband and button from 5-9 pm.

The Nutcracker

Please join us for the 40th annual production of THE NUTCRACKER, a Winchester Holiday Tradition Since 1982!

Tickets are reserved seating. You are able to select your seats using an interactive seating chart. If you have a special seating request or need help selecting seats, please call 540-665-0343. Tickets may also be purchased by cash or check at the studio, 20 West Cork Street, Winchester, Virginia Monday-Thursday 4:00-8:00 pm or by appointment.

Purchase Tickets

Middletown Christmas Parade

Come out and Celebrate the Magic of the Holiday Season with Friends & Family in Historic Middletown, VA on Sunday, December 5, 2021.

The Christmas Parade begins at 2pm with horses, floats, bands and more leading the way for Santa and Mrs. Claus to travel down Main Street. Immediately following the parade we will host Santa with free hot chocolate and cookies at Wayside Inn.

Come early to get a great spot for watching the parade and while you are in town explore the local shops and restaurants.


Model Railroad Show

The Winchester Model Railroad club will be hosting its Fall 2021 sale, Saturday November 13th at the Winchester Moose Club. The sale will open to the public at 9 AM and run until 1 PM. All scales of model railroading are welcome and you never know what will show up on the sales tables. Items from several estates will also be up for sale.

Due to COVID, we will be following the safe guidelines for social gatherings. Social distancing is highly recommended. Admission is $5.00 at the door, bring this flyer with a valid email entered below and receive a dollar off each paid admission.

Admission: $5.00 at the door, 12 and under free!

If you’d like to be a vendor, tables are still available and free. Send an email to WMRRA2016@GMAIL.COM for more information.
Follow us on Facebook for announcements prior to the day of the sale. Cancellations or schedule changes will be posted as soon as possible but no later than 7 PM Friday November 12th.

Pumpkin Festival

Come find the “great pumpkin.” 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.

Free admission.

Richard’s Apple Festival

FREE Admission! Join us on Saturday, October 16, 2021 from 11am – 3pm for our Annual Apple Festival & Farm Party! We’ll have live music, farm food (sliders from our own burger, farm to crust pizza, hotdogs, caramel apples) and of course, LOTS of apples. The wine and beer garden will be open for tastings and flights too.

This is a family friendly event, so bring the kids and spend the day in the country with us! Have fun in our petting zoo, let the kids cruise around in the barrel train, or just run around til they’re exhausted. We’ll have outdoor games like badminton & cornhole too.
The event is rain or shine, bring your umbrella because then it won’t rain!

Be sure to invite your Facebook friends and then bring them along for a great afternoon on the farm.

Apple Harvest Festival

Saturday, Oct. 9 (9am-5pm) & Sunday, Oct. 10 (10am-5pm)
Everything apples!

Multiple varieties of apples to choose from, with pick your own available.

Apple cobbler and apple cider slushees can be enjoyed while sitting on the front porch or listening to the music each day from 1-3 P.M. For the kids we have a playground and room to run. A variety of food will be available at the food building.


French and Indian War Weekend

Join us for a weekend of living history at the French and Indian War Weekend!

18th Century Colonial Encampments

Drilling and Musket Presentations

Two Battle/Skirmishes

Historical Interpretation of Colonial Forces in the French and Indian War

Tours of Abram’s Delight, Winchester’s oldest home

Free admission

Tomato Festival

Join us for Richard’s Fruit Market’s second Tomato Festival!

Come enjoy a day at the farm with live music, great farm food, barrel train rides, pick-your-own flowers, wine and craft beer tasting, and of course, lots of tomatoes!

Free admission.

Shenandoah Valley Apple Harvest Festival

The 2021 Shenandoah Valley Apple Harvest Festival will be held at the Frederick County Fairgrounds, 250 Fairground Rd., Clear Brook, VA.
The festival has always been family (and pet) friendly!

BRING YOUR OWN CHAIR OR BLANKET (please, no ice chests)

Gate admission includes Free Inflatables, Live Music, Apple Pie Eating Contest, Apple Pie Judging Contest, Artisans and Vendors, Canine Challenge Course, Samples, and Classic Car and Hot Rod Show!

CRAFTSMEN & VENDORS…Local and Regional Artisans and Vendors throughout the grounds and two (2) open-air buildings.

KIDZONE AREA with INFLATABLES, PONY RIDES and FACE PAINTING…always popular, always fun! An area just for the kids with a Giant Slide and Obstacle Course. Nearby handwashing station for use before and after play.

CANINE INTERACTIVE CHALLENGE COURSE…on Sunday. Sponsored by Blue Ridge Dog Training Club. This course will engage the canine mind and provide exercise for all breeds, sizes and ages!

CLASSIC CAR & HOT ROD SHOW…Enjoy a great collection of antique vehicles in a festive atmosphere, Saturday at 10:30am.

TAP & CORK (HARD CIDERS & CRAFT BEERS)…Must be 21 and over with ID required. Live entertainment nearby makes this a can’t miss attraction!

APPLE PIE EATING CONTEST HOSTED BY WHITE HOUSE/NATIONAL FRUIT…What would an apple harvest festival be without the popular apple pie eating contest? Center stage, Sunday at 3pm!

APPLE PIE BAKING/JUDGING CONTEST…Saturday at Noon. Anyone can enter! 1st prize is $100, 2nd prize $50. See details and how to enter at

LIVE ENTERTAINMENT… Continuous entertainment featuring Mojo Mothership, Rob Talton, Jimmy Lee, Wayne Lee Ray Band, and others TBA…all family friendly.

FOOD CONCESSIONS… Plenty of EVERYTHING APPLE…Apple Pie, Apple Dumplings, Ice Cream, BBQ, Crab Cakes, Turkey Legs, Burgers, Ice Cream, Kettle Corn, Lemonade and all your festival favorites!

ADMISSION IS DISCOUNTED WITH $1.00 OFF COUPONS THROUGHOUT THE COMMUNITY, including the Winchester-Frederick County Visitors Center and the area HANDY MART stores. Admission includes all activities except adult beverages and Pony Rides. General admission is only $10! Age 10 and under are FREE! MILITARY/VETERANS AND LAW ENFORCEMENT ARE FREE!

IT’S FOR A GREAT CAUSE…Giving back to the community just feels good. Be a part of some-thing big and contribute to this event by exhibiting and/or attending. All proceeds for the event go to local non-profits. Over $1.2 Million Dollars has been given over the life of this event…so thank you!