Charlottesville Fall Bucket List

Fall is in full swing. The leaves are peaking, the temperature is crisp and we are on the cusp of a gorgeous fall weekend in Charlottesville. To help you make the most of this beautiful season here in Charlottesville, we have compiled a list of can’t-miss events, sights, smells, tastes, and experiences recommended by our Scout Guide Charlottesville members for you to enjoy. How many of these activities can you check off your list this season?

#1: Trip to Carter Mountain Orchard

Carter’s Mountain Orchard comes highly recommended by our members, making it a can’t-miss spot this fall! Kristen Rowe, the Neighborhood Nutritionist says: “It’s hard to narrow it down to just one, but my favorite Charlottesville fall activity would have to be picking apples at Carter Mountain Orchard! There’s so many healthy fall treats you can make with their crisp, delicious apples!”

Charlottesville Orthodontics also raved about Carter’s Mountain: “When I think of Fall in Charlottesville, I immediately think of Carter Mountain Orchard and their Apple Cider Doughnuts, the perfect fall view and fall treat!!”

#2: Afternoon at Albemarle Ciderworks

Albemarle Ciderworks is the perfect place to spend a fall afternoon. Megan Giltner of Derriere de Soie says: “Our family loves hanging out at Albemarle Ciderworks on a beautiful fall day – and looks forward to taking home some of their gorgeous heirloom apple varieties to enjoy at home.”

#3: Antiquing around Virginia

The start of a new season is a great time to refresh the decor in your home, and antiquing is the perfect way to find unique pieces. Kristen Martel of Heyday Antiques and Vintage says: “We love to go antiquing in the Fall for all our holiday prep – nothing like spending a weekend shopping with your bestie at all the amazing antique stores between C’ville and Richmond!”

#4: Blessing of the Hounds at Farmington Hunt Club

This activity is sure to be a hit in your family this Thanksgiving. Meg Michaels of Albemarle Staging and Design says: “We love kicking off Thanksgiving morning by tailgating at Farmington Hunt Club’s annual ‘Blessing of the Hounds’ with loads of friends and family!”

#5: Pumpkin Patch at Chiles Peach Orchard

Chiles Peach Orchard is a favorite spot among our members all year long, but it is especially popular during the fall. Ann Hay Hardy of Frank Hardy Sotheby’s International Realty says: “I love Chiles Peach Orchard for their pumpkin patch and yummy fall treats!”

The Lodge at Old Trail also raves about Chiles Peach Orchard: “My favorite fall tradition is pumpkin picking at Chiles Orchard.”

#6: Stroll around Downtown Charlottesville

Fall in Charlottesville is truly a time unlike any other, and a downtown stroll is a perfect way to soak up the beauty of the season. Conor Bredder of Bredder Management says: “My wife and I love to plan the perfect date night on the mall and stroll around Locust Ave. and Park St. at dusk after a nice dinner and, of course, some Chaps! We enjoy looking at the fall color and commenting on all of the classic Charlottesville Architecture.”

Kristen Watson of Pūrvelo says: “When I was still living in Charlottesville one of my favorite things to do was grab an early afternoon coffee from Atlas Coffee and go for a long walk through the Fry Spring neighborhood with my husband and our two dogs… if it wasn’t too chilly we would pit stop over to Fry Spring Station for some snacks on the patio.”

#7: Tour the James River

Lydia Lodge of Be Just Cville says: “We just love this company. Best fall excursion! Experience the magic of the James River aboard the James River Batteau. Their Sunset Cruise brings to life a modern interpretation of the evening river experience. As the sun begins to drop behind the tree line, enjoy charcuterie and refreshments while being serenaded with light acoustic music to the accompaniment of night falling on the river.”

 #8: See a Show at Ting Pavilion

Live music is always a hit, but it is even better on a cool fall night. Megan Kingdon of Well Room says: “Fall is spectacular in Cville so it’s hard to limit it to one!  Fall abounds with all kinds of great activity – Pippin, Potters, Carter Mt, hikes, etc etc but what immediately came to mind was seeing shows at the Pavillion.   It’s especially amazing during this season. We are so lucky to get amazing performers coming through Charlottesville on fall tours.  Being able to see performances at such an intimate venue, especially on a gorgeous Virginia fall night, is pretty special.”

#9: Make the most of fall in Charlottesville

Eleanor VonAchen of the Dairy Market says: “Fall is one of my favorite times of year in Central Va. I love pumpkin and apple picking, cooking all day, taking drives on skyline to see the leaves change, all of it. I love crisp nights at the fire pit with friends and cocktails. Restaurants and shops are buzzing and getting ready for the holidays and people are out and about more. I love Charlottesville, but I think I love it in the fall the most.”

We can’t help but agree. There really is something special about this time of year in Charlottesville. In addition to all of the fabulous recommendations from our TSG members, we have the following items on our Fall bucket list:

Join the last Sunday Polo matches of the season at King Family Vineyards on October 23rd and 30th and enjoy the stunning fall foliage in the surrounding mountains.

Take the kids to the Tots Tuesday: Pumpkin Painting event at the Dairy Market on October 25th.

Enjoy an evening out at The Quirk Hotel Charlottesville on November 2nd with interior designer and author Janie Molster as she discusses her book “House Dressing: Interiors for Colorful Living.”

Attend the Be Just Sunday Supper with Two Fire Table at Fat Cat Farm on November 13th.

Spend a beautiful fall afternoon at Merrie Mill Farm & Vineyard enjoying Sunday Blues & Jazz while sipping wine.

Learn to make a perfect fall comfort meal in the One Pot Wonder cooking class at Pippin Hill Farm & Vineyards on November 17th.

Attend the Thanksgiving Turkey pickup party at Heritage Glen Farms to pick up your locally raised KellyBronze turkey on the Saturday before Thanksgiving. Place your order now to get invited.

Treat yourself to a Modern Tea Service at Cake Bloom on Sunday, November27th.

Schedule a day of Wellness at Well Room to prioritize your health & beat the holiday stress.

Reserve the heated tent at Knights Gambit Vineyard for a cozy date night or fun girl’s night.

Plan a special date night at Marigold at Keswick Hall to enjoy the fall seasonal dishes which celebrate the local fall harvest from Keswick’s own Oakdale farm.