Uncork a Unique Wine Adventure in Charlottesville & Albemarle County!

Pinot and putt-putt? Sounds like a plan! Visit Keswick Vineyards to play the wine-themed, nine-hole minigolf course which features a bar at the halfway point to replenish beverages. Additionally, the winery features an on-site food truck serving light finger foods, and charcuterie Wednesday through Sunday. In early September 2024, Keswick Vineyards opened its Four Seasons Tasting Room, enhancing the guest experience with more covered seating. Keswick Vineyards is located on the Route 231 Trail, a short and scenic drive east of Charlottesville.

Horseback riding through a Virginia vineyard is truly a unique experience. Indian Summer Guide Service creates customized rides at various vineyards along the Monticello Wine Trail. Enjoy a 60-to-90-minute ride through lush landscapes, seeing the vines up close, and taking in the glorious fall foliage all on horseback. After your ride, make your way to the tasting room to enjoy a glass of Central Virginia wine while recounting your adventure. The best part? No previous riding experience is necessary, and rides are available year round, weather permitting.

Sunday polo at King Family Vineyards is a celebrated Charlottesville-area tradition not to be missed! Polo in October is lovely, with cooler temperatures and the stunning Blue Ridge Mountains serving as a perfect backdrop to the action. A free, family-friendly event, attendees choose to tailgate around the field or select a seat on the tasting room patio. Bring your own food or stop by one of the rotating food trucks in attendance each week. In between matches, spectators are encouraged to stomp the divots and enjoy time throwing a frisbee or football. While you’re visiting King Family Vineyards, enjoy a glass of their 2019 Meritage – the winner of the 2024 Virginia Governor’s Cup. You can even reserve a tailgate space in advance for a fee. Please note polo matches are very weather dependent. Be sure to check King Family Vineyards’ website or social media prior to heading out.

Transport yourself to a warmer climate without leaving Virginia during a visit to Glass House Winery. Sip their fantastic wines while sitting amongst the flora in the all-glass conservatory. To add to the unique flavor, Glass House Winery offers handcrafted chocolates made by their in-house chocolatier. Name a better combination than wine and chocolate…we’ll wait.

Kick off Virginia Wine Month with a celebration of exquisite Virginia wines at the Red Wine Showcase on Friday, October 4 from 6:30 - 8:30 p.m. Set against the picturesque backdrop of Eastwood Farm & Winery, this exclusive event brings together 17 esteemed wineries from the Monticello Wine Trail for an unforgettable celebration of red wines. This is a ticketed event, so grab yours today!

Visit the only certified-organic vineyard and winery in Virginia – Loving Cup Vineyard & Winery. Located in North Garden and open Friday through Sunday, guests can taste their small-batch wines made entirely of grapes from their family-run vineyard. These grapes are grown utilizing organic practices, free of synthetic substances. A trip to Loving Cup is worth the wine and the educational experience. In addition to being the only certified-organic vineyard in Virginia, they are one of only three on the east coast of the United States.

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 will make your way to the safari tent for lunch and tasting of Merrie Mill’s single varietal wines. Offered seasonally, the vineyard safari and lunch is available by reservation only for up to 10 guests.

Looking for a transportation company to take your group around the Monticello Wine Trail for an unforgettable day of tastings? Take a Tipsy Wagen wine tour and travel to the tasting room in style aboard a vintage Volkswagen bus named Mable. In this case, the journey is just as great as the destination. Public and private tours are available.

Immerse yourself in the local wine culture with an overnight stay at a Charlottesville-area vineyard. Approximately a dozen of the wineries on the Monticello Wine Trail offer on-site lodging for the ultimate Virginia Wine Month getaway. Sweet dreams, indeed!

Even though Virginia Wine Month is technically over after October, we love a reason to keep the celebrations going! So join the Veraison Project and Oenoverse for the 3rd annual Two Up Wine Down Festival on Saturday, November 2nd on the lawn of The Jefferson School City Center. Get ready for an afternoon of tastings, DJ-spun beats, and an all-star cast of Virginia wine curators. This is a ticketed event, so please plan accordingly.

As you can see, there are plenty of unique wine experiences to be had in Charlottesville & Albemarle County during Virginia Wine Month this October. But the fun doesn't stop there! October is a perfect month to enjoy the great outdoors, fall foliage, events, festivals, and our dynamic culinary scene. With so much to do, you'll want to stay multiple nights to take in all the area has to offer. With a wide selection of hotels, resorts, inns, and bed and breakfasts, there is no shortage of lodging options to be had. PRO TIP: Consider a weekday stay for better rates and greater availability. We can't wait to welcome you this October. Cheers!