1. Play Putt-Putt at Keswick Vineyards

Pinot and putt-putt? Sounds like a plan! Start at Keswick Vineyards to play their wine-themed, nine-hole mini golf course. Tickets are available for purchase in the taproom! While you're there, grab a bite from their on-site food truck, Barrel & Board, which serves light finger foods, sandwiches, and charcuterie boards every Wednesday through Sunday from 12-5PM.

2. Explore a Vineyard on Horseback

Horseback riding through a Virginia vineyard is truly a unique experience you won't want to miss out on. Indian Summer Guide Service offers custom rides at various vineyards along the Monticello Wine Trail. Enjoy a 60-to-90-minute ride through lush landscapes with the beautiful Blue Ridge Mountains in the background. After your ride, make your way to the tasting room to enjoy a glass of Central Virginia wine while recounting your adventure. No previous riding experience is necessary, and rides are available year-round, weather permitting!

3. Tailgate at a Polo Match

Sunday polo at King Family Vineyards is a celebrated Charlottesville-area summer tradition not to be missed! Polo in October is especially lovely, with cooler temperatures and the stunning Blue Ridge Mountains serving as a perfect backdrop to the action.

Bring your own food or stop by one of the rotating food trucks in attendance each week. This even is first-come, family-friendly, and free. For an elevated experience, skip the line and reserve a tailgate space in advance! Please note: polo matches are weather dependent -- be sure to check King Family Vineyards’ website or social media prior to heading out.

4. Visit the Tropics at Glass House Winery

Transport yourself to a warmer climate at Glass House Winery & Brewery. Their glass conservatory is home to over 300 plants and naturally maintains a warm temperature in the colder fall months. It's truly a one-in-a-lifetime experience!

5. Head to Eastwood After Dark

Every Saturday night, Eastwood comes alive with upbeat, dance-worthy bands in a lively, laid-back setting! Music starts at 5PM and ends at 8PM. Here's the lineup this fall:

6. Visit Virginia's Only Certified-Organic Winery

Discover Loving Cup Vineyard & Winery, the only certified-organic vineyard in the state and only one of three on the East Coast. Open Friday through Sunday, this family-run vineyard crafts small-batch wines exclusively from grapes grown using organic practices—completely free of synthetic substances. 👉 Learn More About Loving Cup's Organic Methods

7. Go on a Wine Safari at Merrie Mill Farm & Vineyard

Climb aboard a vintage Land Rover to experience a vineyard safari at Merrie Mill Farm & Vineyard. Your guide will take you on a tour of Merrie Mill’s hillside vines, stopping to educate your group on the nuances of viticulture and the winemaking process. You'll then make your way to a safari tent for a lunch and tasting of Merrie Mill’s single varietal wines. 👉 Learn More and Book Your Safari

8. Sip and Stay: Your Ultimate Vineyard Getaway

Take your Charlottesville wine experience to the next level with an overnight stay at a local vineyard. Nearly a dozen wineries along the Monticello Wine Trail offer on-site lodging, letting you wake up to scenic vineyards, enjoy morning tastings, and fully immerse yourself in Virginia wine country. PRO TIP: Consider a weekday stay for better rates and greater availability.

Places to Stay Charlottesville and Albemarle County offer visitors a wide variety of places to stay, including resorts, hotels, inns, bed and breakfasts, cabins, and vacation rentals. Learn More
Things To Do in Charlottesville & Albemarle County There's plenty to do in Charlottesville and Albemarle County, no matter the season! This area boasts world-renowned historic sites, scenic parks and waterways, fun activities for families, vibrant arts and culture and great shopping spots. Learn More
Outdoor Recreation If you love hiking, kayaking, and the great outdoors, bring your love to Charlottesville and Albemarle County, where outdoor enthusiasts can adventure at every altitude and speed! Recently voted a 2024 Top Adventure Town by Blue Ridge Outdoors Magazine! Learn More
Food & Drink With an incredible array of restaurants per capita, the Charlottesville food scene boasts big city dining rooted in small town charm. Learn More
Wineries Welcome to the birthplace of American wine. Charlottesville and Albemarle County are home to more than 40 wineries along the Monticello Wine Trail, offering visitors lush views and a dynamic wine scene in the heart of Virginia. Learn More

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