Fall Charlottesville Guide

Summer has sundresses and sandals, but fall has tall boots and snuggly sweaters and who doesn’t love all that? Check out this round-up of Charlottesville boutiques with sweaters and other warm, comfy clothes that will help you keep the chill at bay.


Did you know Country Roads isn’t actually about West Virginia, it’s about Western Virginia? And honestly, it could have been written about Western Albemarle- “Blue Ridge Mountains, Shenandoah River…” Just saying. If you want to get to know those infamous spots a bit better, Charlottesville is your best bet. Whether you want an hour of sweating it out for some prime views, or a day of soaking up rays on the river, you’ll find it here.

1. Summit

C’villians are hikers, plain and simple. In the early fall, most porches in town are littered with a collection of slightly muddy boots, and the Instagram feeds are full of the young and young-at-heart, hands to the sky on the edge of their favorite peak. To join them, take the quintessential Charlottesville hike up Humpback Rocks. It’s a short, deceptively steep climb with plenty of spots to stop. Pack a picnic lunch and a DSLR, and you’ll be posing above the birds in no time.

2. Get on a Boat or Go for a Float.

Speaking of that Shenandoah- Charlottesville has more rivers than most of the locals can keep track of. We’ve got the James, the Moormans, the Rivanna, the Rappahannock, the Rapidan, and two forks of the Shenandoah within an easy drive. With so much water, it’s almost criminal to not enjoy it. There are two major river trip guides- James River Rafting down in Scottsville, a favorite for relaxing tube floats and whitewater rafters, and Rivanna River Company, best for kayaks, canoes, and in-town trips. Rivanna River Co even has a “paddle to pints” trip, finishing up in the heart of town at Random Row Brewery. After all, who doesn’t need a beer after a day on the river?

3. See the City on Two Wheels

Charlottesville is a bicycle-friendly city. There are just about as many bike lanes throughout the city as there are sidewalks. Blue Ridge Bicycle Tours offers tours of the historic city of Charlottesville and the University of Virginia. They can also create a custom tour for areas in which you've always wanted to visit. Group events, such at team building or corporate outings, are available, as well.

4. Go Up, Up, Up!

Plenty of open fields and spectacular views make Charlottesville uniquely suited to balloon aeronauts. Monticello Country Ballooning offers sunrise flights for the early birds, sunset flights for the romantics, and includes a champagne toast with every flight so you can welcome the day— or the night— in style.

5. Fall Out of the Sky

Please don’t confuse this one with the ballooning trip. A few miles down the road from Charlottesville, you’ll happen upon an airstrip and a couple of hardened adrenaline junkies packing their chutes. If you’re looking to knock something off your bucket list and get a totally unbeatable view of Virginia, head over to Skydive Orange (with reservations!). If you go for a later jump on a Saturday, you might get a chance to hang out by the firepit after hours and hear some truly unbelievable stories from the sky.

6. Beach It

Believe it or not, Charlottesville has a beach. No, the Atlantic didn’t take a surprise trip inland- our sandy shores are lakeside. About 15 minutes down Route 20, you’ll find Walnut Creek Park, with two acres of sand beach ready for you and yours to lay down towels, chairs, and sandcastle building kits.


Summer has sundresses and sandals, but fall has tall boots and snuggly sweaters and who doesn’t love all that? Check out this round-up of Charlottesville boutiques with sweaters and other warm, comfy clothes that will help you keep the chill at bay.



The Blue Ridge Mountains in fall are a magnificent sight to behold, and Charlottesville is the perfect place for autumn sight-seeing. The leaves turn in October, and you can take in the visual spectacle by car or on foot, and even with a glass of local beer or wine in hand.

Six Fall Picks - Pumpkins Galore!

Carter Mountain Orchard

Carter Mountain Orchard is a Charlottesville favorite, just minutes from downtown Charlottesville and offering stunning views of the city.  Enjoy the festivities of the season - fruit picking, pumpkins, hayrides, live music, and family fun events as well as food and drink - apple cider, baked goods, Carter Mountain Wine, Bold Rock Cider on tap, and last but not least..their famous apple cider donuts!

Come wine, dine and have a good time!

Chiles Peach Orchard

Within reach of charming downtown Crozet, pick your own fruit and pumpkins surrounded by beautiful views of the Blue Ridge Mountains. Make a day of roaming through the seasonal fruit and veggie picking then head on over to the Farmers Market for sweet treats and wine! Check out their festive calendar of events!

Have you tried apple cider donuts?

Liberty Mills Farm

Visit the largest corn maze in America located about 25 miles northeast of Charlottesville, in Somerset VA!  Don’t miss out on seeing this masterpiece in nature, and marvel at the time and effort put into its creation.  And, pick your own pumpkin and check out their farm market while you’re at it!

The Corner Store Garden Center

Take a beautiful fall drive to the Corner Store Garden Center located just north of Charlottesville in Ruckersville, VA.  Shop for pumpkins, fall plants, and decorations, and enjoy fun family events and festivities like pumpkin painting and their Fall Makers Festival featuring live music, food, and local artisans, and make your own flower bouquets!

Blue Ridge Mountain Maze at Blue Toad Hard Cider

Experience fall festivities for the entire family!  Located in Roseland, VA at Blue Toad Hard Cider, they offer an array of fun activities including a 5-acre corn maze, giant slides, apple slingshot, farm animals and pony rides, pumpkins, hot cider, kettle corn, apple cider donuts, fresh squeezed lemonade, country store and a whole lot more.  And the best part, mom and dad can sip on a cider and relax after the kids have had their fun! This is a “must go” if you’ve never been!

Critzer Family Farm

Located in beautiful Afton VA, bring the whole family and enjoy a few hours in the Blue Ridge!  Pick out a pumpkin and have some pumpkin ice cream and cider, then head across the street to Blue Ridge Brewery for dinner and beer!

Pick your pumpkins, apples, and blackberries!