Top 10 Must-Do List for Fall Around Winchester

Fall starts in the Northern Shenandoah Valley in September, and every year the communities of Winchester and surrounding Frederick County gear up for the many travelers that come through from all over the region, nation and world. Just like in 2020, this year it feels like everyone is looking to explore more and stay outside. Fortunately our unique experiences, great local markets and businesses are open and are ready to safely welcome everyone as new friends when they arrive.

Viewing our fall foliage is such an integral part of any trip here this time of year, we’ve just put an icon next to leaf-peeping related opportunities.

Our team has compiled a Top 10 list of Winchester area things you just can’t skip when visiting every year as the nights get cooler, the weather gets calmer, and our outdoor beauty comes into sharp focus.  Get out and enjoy!

#1 – Go to a farm market

Richards Fruit Market
Image of Richards Fruit Market, property of Winchester-Frederick County Tourism

This season is their bread and butter, and for good reason.  You’ve got the big, ever-popular ones like Marker-MillerVirginia Farm Market, and West Oaks Farm Market and then some really unique and fun smaller finds like Hill High Farm, the Homestead Farm at Fruit Hill OrchardRichard’s Fruit Market, Rinker Orchards, Virginia Farm Market, and Shen Val Farm Market!

#2 – Turn off that GPS and go for a country drive 

Image property of Winchester-Frederick County Tourism

Yes, I’m telling you to get lost (but seriously, in a friendly way) out on our local roads.  We’ve got fields, orchards, rolling hills and mountains all within about 20 minutes of Old Town Winchester.  Or if, like many of our fall visitors, you’re headed to the nearby Skyline Drive in the Shenandoah National Park, take a side road like 522 or 11 and enjoy the ride down and make a few discoveries along the way.

#3 – Roll up your sleeves and pick an apple 

Image of Marker-Miller Orchards, property of Winchester-Frederick County Tourism

Surprise, this is apple country.  I know you probably already knew that, but to really grasp the scale of it you’ve got to actually get into the trees at one of those orchards.  Marker-Miller, West Oaks and Rinker Orchards have pick-your-own operations, or just drive around the countryside and look for some “pick-your-own” signs.

#4 – Hike or mountain bike to a vista point, even if just for an hour or two

Image of Eagle Rock on the Tuscarora Trail, property of Winchester-Frederick County Tourism

The Tuscarora Trail is truly a hidden gem, but may not remain so once people realize there’s alternative for Old Rag to get beautiful valley vistas.  We’ll make it easy for you to get magnificent views of our fall foliage – get to Eagle Rock overlook by clicking HERE and hiking about 1.75 miles northeast along the trail, or get to Pinnacle Rock (pictured) by clicking HERE and hiking from the Biby Trailhead.  Need maps, gear, or just some local expertise?  Then Mountain Trails Outfitters on the Old Town Walking Mall is a necessary stop. There are many miles of mountain biking trails in the George Washington National Forest, through which the Tuscarora Trail runs. Check out Element Sports in town for local expertise, maps and gear.

#5 – Enjoy a meal al fresco

Image of Old Town Winchester Loudoun Street Mall, property of Winchester-Frederick County Tourism

This was our our lastest blog, but it was still a little warm when we posted it.  The evenings are perfect now – check out the list, choose at least one and enjoy!

#6 – Go on a horseback trail ride 

Image of Rocking S Ranch, courtesy of Rocking S Ranch Facebook Page

Okay, we’ve got lots of options regionally for trail rides, and there’s a reason for that.  Our surrounding countryside in the Shenandoah Valley provides an incredible trail ride experience.  This is a must-do for young and old alike.  Check out our professional trail ride outfitters such as Bailey’s Walking After Midnight FarmMagic Mountain Farm or the Rocking S Ranch (the #1 rated local attraction on Winchester’s TripAdvisor page).

#7 – Have a local, seasonally brewed pint of beer or cider

Alesatian Brewing
Image of Alesatian Brewing Co, property of Winchester-Frederick County Tourism

In the very recent past, you couldn’t get a pint of locally crafted beer here.  Now we’ve got four different, unique and pretty awesome brewery options and an outstanding cidery.  Alesation Brewing Company, Broken Window BrewingWinchester Brew Works, Escutcheon Brewing Co. and Winchester Cider Works all have great fall offerings and on-site tastings.  These are all sites along the Shenandoah Spirits Trail, which pulls together every brewery, winery, cidery and distillery in the Northern Shenandoah Valley. Want traditional non-alcoholic apple cider?  You’ll find it at most local markets – Rinker’s apple cider is pretty famous.

#8 – Catch a show under the stars at the drive-in

Image of Family Drive-In Theatre, property of Winchester-Frederick County Tourism

There are only seven drive-in theatres left in all of Virginia, so the Family Drive-In located just outside Stephens City is truly a special place. Open throughout the fall season (not just summer!) and offering special screenings of classic films.

#9 – Get off-road and a bit dirty, then take a mountain dip

Image of Appalachian Offroad Adventure property of Winchester-Frederick County Tourism

The Cove Campground offers over 40 miles of off-road trails set in a 3,000 acres mountain playground. You can bring your own 4×4 vehicle to ride the trails, or jump behind the wheel of one of the Jeeps from Appalachian Offroad Adventure. After an orientation ride, you get to drive on a guided half or full day tour on the trails. Afterward, if the day is still warm, relax on the sandy beach at their largest lake.

#10 – Challenge Yourself to a Corn Maze 

Image of the West Oaks corn maze, property of Winchester-Frederick County Tourism

Check out the traditional maze at the Pumpkin Patch at Hill High Farm, the massive annually-themed maze at West Oaks Farm Market, or the scavenger hunt corn maze at the Pumpkin Patch at Edge-Wood Dairy. Each is as unique as the farm markets that they are attached to!


As always, no business or individual paid to be on this list – it’s just a fun collection of some top fall activities that should keep you busy for this fall, and probably next fall as well!  Don’t be shy to let us know if we missed anything!.