Absorbing sun-soaked vineyard views, sampling flights of wine and peeking behind the curtain at the winemaking process — the typical group visit to a winery is already enchanting. But if a group is full of oenophiles or if the destination is an award-winning wine region, going the extra mile to arrange an especially immersive activity or tour is often worth it.
Whether your travelers like their wine crisp and bubbly, dry and rich, or light and sweet, here are five distinct experiences that are sure to make a splash.
Horseback Riding Vineyard Tours
Charlottesville, Virginia
The Charlottesville area was named Wine Region of the Year by Wine Enthusiast in 2023, and for good reason. The area’s 40-plus vineyards are producing award-winning wines, and the Monticello Wine Trail, comprising more than 30 wineries, is drawing notice from tourists and critics alike. While visiting any combination of these vineyards is sure to delight groups, one tour operator is offering a more hands-on look at the grapes.
Indian Summer Guide Service has been giving horseback tours of vineyards in Charlottesville since its founding in 2010. The experience begins with a ride through the vineyard that lasts from an hour to 90 minutes. Then, the group heads back to the winery for a tasting or a glass of wine. Ashton Beebe, founder and owner of the tour service, said the company prioritizes quality over quantity by giving small group tours of six to eight, making it feel less like a standard trail ride.
“We don’t make our clients go nose to tail,” Beebe said. “Keeping it as a small, private experience makes people relax more. People come as strangers and leave as family.”
Large groups can be divided, with some enjoying the wine tasting experience first while they take turns riding through the vineyards. The experienced guides and small groups make it a good option for groups with first-time riders. The most popular time of the year for one of these wine tours is autumn, when the weather is cooler and the Blue Ridge Mountains and vineyards turn vibrant shades of gold, orange and red.
Groups can choose from several local wineries to tour, including Veritas Vineyard and Winery, Merrie Mill Farm and Vineyard, Cunningham Creek Winery, Pollak Vineyards, Chiswell Farm and Winery, and Keswick Vineyards. In addition to vineyard tours, Indian Summer Guide Service also offers tours of a few local cideries and breweries.
Winemaker for a Day
Napa Valley, California
One of the most famous wine regions in the world, Napa Valley features several picturesque towns and hundreds of vineyards, wineries and tasting rooms. This California county has an abundance of wine experiences, ranging from conventional tastings to amped-up excursions synonymous with luxury.
One such experience can be found at Raymond Vineyards, a member of the Boisset Collection, a prestigious group of brands found at a handful of wineries around Napa Valley. Raymond Vineyards, in St. Helena, was founded in 1970 and has been prominent in the area ever since. Today, it’s known for its luxurious tasting room and its high-quality wines, including its cabernet sauvignon, merlot and chardonnay.
But in addition to its standard tasting experiences, the winery also offers a more hands-on opportunity for groups to learn about wine and its production. The Winemaker for a Day experience allows groups unprecedented access to the wine-making process. They’ll spend their time in the winery’s blending room, learning about wine and creating their own Bordeaux-style red blend. Once they’ve created a blend to their liking, the winery will bottle it, cork it and even create a custom label for the bottle. Visitors can take it home that day, and the winery can even produce cases of their custom blend. Groups of up to 12 can reserve this exclusive experience.
Wine Train and Tour
Ringoes, New Jersey
It may come as a surprise to learn that New Jersey is increasingly earning recognition for its wines. While perhaps not the most famous wine region on the East Coast, the Garden State has been producing a respectable range of varietals in its four different growing regions, from chardonnay and riesling to sweeter wines. One of the best ways for a group to experience New Jersey wine combines antique train travel with more traditional wine experiences.
The Hunterdon Wine Express is the product of a collaboration between the historic Black River and Western Railroad, a volunteer-run organization dedicated to the upkeep of the antique train in Flemington, and Old York Cellars, a winery in Ringoes. Every stage of the wine production process happens at Old York Cellars, from growing the grapes to bottling the wine.
“The wine train offers an experience that goes beyond the grape,” said Karin Colantuono, marketing manager at Old York Cellars. “It’s a unique experience taking a classic train through our bucolic countryside. Then for the tasting, you’re right in the vines. You really get that immersive experience.”
First, the group boards the historic train at the station in Flemington. Once the train departs, an Old York Cellars representative begins telling the winery’s story as guests enjoy beautiful views of the New Jersey countryside. When they arrive at the station in Ringoes, they’re shuttled to the winery for a charcuterie and tasting experience of six wines. Then, they’ll enjoy lunch at the winery and look around the vineyard before being shuttled back for the return trip.
The train’s capacity is 49 passengers, and excursion dates are coordinated with the railroad based on volunteer availability. However, private events are considered on a case-by-case basis.
Grape Stomping at a Harvest Festival
Fredericksburg, Texas
In a state as large as Texas, the wine produced varies greatly based on weather and region. However, Fredericksburg and the surrounding Texas Hill Country have earned a reputation as the state’s preeminent wine region. To spend a day immersed in the local wine — literally — groups can take part in a grape stomp at a local winery.
One grape-stomping opportunity comes around harvest time at Messina Hof Winery, which was founded in 1979 and now has several locations in the area. It produces wine from Texas-grown grapes and is known for its port, cabernet sauvignon, sagrantino, riesling and chenin blanc. But it also offers quite a few activities to go along with the vintages. These include grape stomping and grape picking at several of their locations. At the Estate Winery in Bryan, grape picking and stomping are available the first four weekends in August. It’s also an offered activity at the harvest festival at the winery’s location in Fredericksburg, which is held the last weekend of August.
At the Estate Winery, groups can pick the grapes, then stomp them and press their feet into a T-shirt. Four to five people can fit in each stomping bucket, and it’s an activity guaranteed to generate laughter. Then they’ll enjoy a tasting and tour and can even opt for an additional dining experience. Groups larger than 10 get a discounted rate.
“It’s a very bucket-list unique experience that goes well beyond just having a wine tasting,” said Gina Graves, marketing manager at Messina Hof Winery. “It’s a very casual way to approach wine. Sometimes people view wine as stuffy, but this is fun.”
Farm-to-Table Wine Dinner
Wilsonville, Oregon
The Willamette Valley is Oregon’s signature wine region. Located on roughly the same latitude as the lauded wine region in Burgundy, France, its prize varietals include pinot noir and chardonnay. It’s also a region known for abundant agriculture, thanks to its plentiful rain.
That’s where The Kitchen at Middleground Farms comes in. This recreational cooking school located on a 17-acre farm in the Willamette Valley emphasizes cooking with fresh, seasonal ingredients produced on the farm. Once a month (and twice in May, which is Oregon Wine Month), the farm hosts Winemaker’s Dinners, where they partner with a specific winery in the Willamette Valley.
“We go out and taste through all of their wines to determine what we want to focus on, because we want guests to learn about pairing,” said Jessica Hansen, owner, founder and chef of The Kitchen at Middleground Farms. “We pick the wines, then we create a tasting. We are intentional about showcasing the wine.”
Groups can mosey through the farm to see its livestock and its produce while enjoying a welcome beverage, then enjoy a five-course, farm-to-table meal. Each course is perfectly paired with a wine. They’ll learn about the food and wine and even have access to the winemaker to learn more about the process from grape to glass.
“People like to meet the winemaker,” Hansen said. “To get access to the winemaker is unique. That’s what makes these special.”
Wine dinners max out at 30 guests, but the farm offers an abundance of other experiences, from group cooking classes to private events to a small wine festival highlighting the region’s great wineries.
