8 of Winchester’s Can’t-Be-Missed Fall Festivals of 2019

As summer comes to a close and schools are back in session, don’t expect there to be a shortage on things to do in the area. As we welcome in the time of breezy weather and leaf-covered grounds, make sure to keep an eye on these eight fall festivals. What better way to say goodbye to summer than by celebrating the approaching autumn.

Blog post by Winchester-Frederick County Tourism intern, Paige Bridgeforth

Shenandoah Valley Apple Harvest Festival

Start off autumn right with this local favorite! The Shenandoah Valley Apple Harvest Festival is a two-day event that takes place on Saturday, September 21, 2019 from 10am-5pm and Sunday, September 22, 2019 from 10am-5pm. With the attendance growing further into the thousands each year, you can expect all the fun fall elements that have made it such a huge hit – plus new activities that have not been done before! To get your apple fix, make sure to be there for the apple pie eating contest on Sunday at 3pm, the apple pie baking contest, or the on-site apple butter making station. For the kids, look for the newly added Bubbleball by Wonderfly Games on Sunday from 12pm-5pm or the kidszone area with inflatables. Pets are welcome at this festival too, so bring them along to enjoy the canine obstacle course on Saturday. All proceeds made at the Apple Harvest Festival are donated to local non-profits. Find a full list of all this festival has to offer here.

250 Fairground Rd, Clear Brook, VA 22624

Winchester Brew Works Fall Festival

Welcome in the new season with the release of Winchester Brew Works traditional German Oktoberfest lager. Winchester Brew Works will be hosting a fall festival October 5, 2019 from 12pm-6pm to unveil their new lager and to serve up local fall-style beers. If lagers aren’t your thing, don’t worry! There will also be IPAs, ciders, and wine to offer a wide selection. Pair your beer with great food. Crash-Test Yummies will be on site serving German-style food all day. Stop by for a relaxing, chill day full of pumpkin beer and German cuisine.

2504 N Frederick Pike, Winchester, VA 22601

Marker-Miller Orchards Farm Market Apple Harvest Festival

Join Marker-Miller Farm Market on Saturday, October 12, 2019 from 9am-5pm and Sunday, October 13, 2019 from 10am-5pm in welcoming the harvest into town. Everything under the sun to do with apples is going to be there including apple cobbler and apple cider slushees. With over 20 varieties of apples, you can walk the orchards while picking your own, or you can buy a bushel from the market. While enjoying all of the apple treats the market has to offer, listen to the live music that will be playing from 1-3pm. While you enjoy the music, kids can have fun with the cow train, playground, and wagon rides running all day long.

3035 Cedar Creek Grade, Winchester, VA 22602


Photo courtesy Old Town Winchester

A German invasion is happening in Old Town Winchester on Friday, October 11, 2019 from 5pm-11pm and Saturday, October 12, 2019 from 12pm-8pm. This annual festival brings alive the traditions of the Bavarian culture. While walking the Loudoun Street Mall, expect to see street performers, free caricature paintings, a free photo booth, and live music by the Continentals. New attractions to the festival this year are a keg tapping ceremony with Austrian horses and the first ever Bürgermeister crowning. Don’t forget your lederhosen or dirndl for the best dressed contest! General admission is free, but for tastings you must buy a package. The online advanced tasting package is $20 which includes six tastings and a 12 oz glass beer stein. The day-of tasting packages are $25 which also include six tastings and a 12 oz glass beer stein.

136 S Loudoun St, Winchester, VA, 22601

Peak Leaf Music & Brewers Festival

Photo Courtesy of Peak Leaf Music & Brewers Festival’s Facebook Page

Want to know what’s better than enjoying a craft beer with some live music? Enjoying that craft beer with live music to support a great cause. The Peak Leaf Music & Brewers Festival in Middletown, VA is a one day festival on October 19, 2019 that brings together live music, local brews, and food to help kids in this area. A portion of the proceeds go towards providing under-served students in the Frederick County area with school meals. Tickets can be purchased online for $35 and kids under 12 are free. Gates for parking open at 10:30am, but the gates are open to the public at 11am. The live music ends at 7pm, but the festival will close at 8pm. For a full list of musical acts and vendors in attendance, check out their website.

Corner of State Rt 634 and Rt 11, Middletown, VA, 22645

Richard’s Fruit Market Apple Festival

Richard’s Fruit Market of Middletown, VA will be hosting their yearly Apple Festival on Saturday, October 19, 2019 from 11am-4pm. This festival will have yard games, yummy farm to table concession stand, hay wagon rides, a petting zoo, and live bluegrass music playing from 12pm-3pm. It is free to get into the festival, however prices will vary on concession stand products or anything the market has to offer.

6410 Middle Rd, Middletown, VA 22645

West Oaks Farm Market’s Fall Festival

Join West Oaks Farm Market for their second annual Fall Festival, the best festival of the year! The festival will be held on October 19, 2019 from 9am-6pm, and is for all ages. Families welcome! Expect a wide variety of activities from a corn maze, a pumpkin patch, hayrides, an apple cannon, a bounce house, face painting, and much more. From 1pm-5pm, one of Winchester’s favorite local bands, Trainwreck, will perform.

4305 Middle Road, Winchester, VA, 22602

Ravenwood Faire

Calling all knights and maidens! Winchester, VA is getting their first ever renaissance fair at the Frederick County Fairgrounds on October 26 and 27, 2019 from 10am-7pm. This fair is jam packed with everything medieval including fire dancers, jousting knights, drum circles, Celtic dancers, theatrical shows, and live music by Merlin’s Beard. Crafters like Adventure Armoury and American Highlander Kilts will be present to help you dress the part. Local food vendors such as BroBears, Ambrosia Catering, and Creative Concessions will provide enough food for a hearty feast. Fill up your chalice with selections from locals like Winchester Brew Works, Alesatian Brewing, Escutcheon Brewery, Winchester CiderWorks, and Misty Mountain Meadworks.

250 Fairground Road, Clear Brook, VA 22624