Winter brings a refreshing change of pace to the Shenandoah Valley, and there’s no better time to enjoy a relaxed weekend exploring the best breweries in Lexington. With its walkable downtown, historic character, and mountain views in every direction, Lexington has quietly become a standout destination for craft beer lovers.
The breweries in Lexington reflect the agricultural roots of the Shenandoah Valley, producing beers that feel local, intentional, and easy to enjoy. A weekend here might include an afternoon strolling Main Street, popping into independent shops, and settling in at a brewery for a well-earned pint before dinner. Devil’s Backbone Brewery is often at the top of the list, offering flagship beers alongside seasonal releases in a spacious, welcoming setting. Heliotrope Brewery adds another layer to the experience with thoughtfully crafted ales and lagers paired with artisan pizza, making it a favorite stop for a casual evening out.
Just outside of town, Great Valley Farm Brewery and Winery is a natural addition to your itinerary, especially if your plans include a visit to Natural Bridge. The views are impressive, and the relaxed atmosphere invites you to linger a little longer. Rockbridge Vineyard and Brewery, located between Lexington and Staunton, rounds out the experience with a mix of beer and wine that highlights the region’s versatility.
After a day spent exploring breweries near Shenandoah National Park, having the right place to unwind makes all the difference. Our luxury Shenandoah Valley bed and breakfast and cabins offer a peaceful mountain setting just minutes from Lexington and Staunton. Whether you prefer a private cabin or a classic inn stay, our 50-acre property is designed for couples seeking an easy, unhurried weekend away.
Beyond the breweries, there are plenty more things to do in Lexington, from scenic drives to historic sites and nearby hiking trails. A weekend here is about balance, good beer, great scenery, and a place that invites you to relax fully. Book your stay and experience why our inn is one of the best places to stay near Lexington for a brewery-focused weekend getaway.
The Kentucky Bourbon Trail offers couples a well-paced blend of scenic drives, historic distilleries, and immersive tastings across the state’s rolling countryside. With more than 40 participating distilleries in Kentucky, the experience combines craftsmanship, regional heritage, and a structured way to explore some of the most recognized names in American bourbon.
A thoughtful Kentucky Bourbon Trail itinerary typically spans three to four days, allowing time to appreciate each stop without feeling rushed. Bardstown serves as an ideal starting point, with nearby distilleries such as Heaven Hill, Willett, and Bardstown Bourbon Company offering a mix of traditional and modern approaches. Between tastings, visitors can explore the best things to do in Bardstown, where you’ll find boutique shops, galleries, and restaurants.
Continuing your route, Maker’s Mark in Loretto stands out for its picturesque grounds and signature bottle-dipping experience, while Jim Beam offers a broader look at large-scale production. Toward Frankfort and Versailles, Buffalo Trace and Woodford Reserve highlight two distinct sides of bourbon production, from historic campuses to refined tasting environments. For those including Louisville, distilleries such as Old Forester, Angel’s Envy, and Michter’s offer a walkable, urban contrast.
Understanding what makes bourbon unique enhances the experience. Kentucky’s limestone-filtered water and seasonal temperature shifts play a key role in shaping flavor, while barrel aging adds complexity over time. Booking tours in advance is essential, and limiting visits to two or three distilleries per day helps maintain a relaxed pace.
Choosing the right accommodations is key to completing your Kentucky Bourbon Trail experience. The best romantic getaways in Kentucky combine proximity to top distilleries with a setting designed for comfort and privacy. Maple Hill Manor offers a restored estate atmosphere where couples can unwind after a day of tastings.
Guests can enjoy thoughtfully appointed rooms, quiet common spaces, and curated packages that simplify planning. Options may include customized itineraries, distillery tour tickets, dining credits, and bourbon-themed amenities that enhance the overall trip. For added convenience, private chauffeur services allow couples to explore the Bourbon Trail without managing transportation.
With the right balance of planning and flexibility, the Kentucky Bourbon Trail becomes more than a tasting tour. It is a complete couples getaway that blends discovery, relaxation, and time spent in one of the country’s most distinctive regions. Reserve your stay and begin planning your itinerary today.
If a weekend built around good wine, cold beer, and rolling countryside sounds appealing, the Mercer County Wine and Brew Trail delivers exactly that. Tucked into northwestern Pennsylvania, Mercer County is home to a growing lineup of family-owned wineries, craft breweries, and small-batch distilleries, most of them within a short drive of one another. The trail runs along two loops: a Northern Lake Trail past Pymatuning, Conneaut, and Lake Wilhelm, and a Southern Amish Countryside Trail through the farmland south of Mercer. Along either route, expect Amish buggies, working farms, and views that are especially good in the fall.
Because Mercer County sits just off I-79 and I-80, it makes an easy weekend trip from Pittsburgh, Erie, Cleveland, or southern Ontario.
Pennsylvania wineries in this area each bring their own character. Dock Side Cellars in Clark sits on Lake Wilhelm and happens to be right next door to Tara – A Country Inn, making it an easy walk from your room to a glass of wine at the water’s edge. Conneaut Cellars Winery & Distillery in Conneaut Lake crafts wine and spirits on-site, shaped by the Lake Erie microclimate. Wilhelm Winery & Antique Wine Making Museum in Hadley pours tastings inside a century-old barn, and Gatehouse Winery in Jamestown sits on 100 quiet acres. Round out the day with Webb Winery in Hermitage, Nova Cellars Winery in Pulaski, Fractured Grape Wine Cellars in New Wilmington, or Knockin Noggin Cidery & Winery in Volant.
Cobblehaus Brewing Co. by the Falls in Mercer overlooks Springfield Falls and pours beers inspired by German and Belgian traditions. Mortals Key Brewing Company near Pymatuning State Park keeps things easygoing and artistic, while Brew 32 Craft Brewery in Pulaski pours ten beers on tap with live music on Friday nights. Hop Asylum Brewing sits in walkable New Wilmington; Big Rail Brewing pairs well with a stop at Grove City Premium Outlets; and TimberCreek Tap & Table in Mercer works as a full-meal stop. For spirits, try Lynchwoods Spirits, MLH Distillery, or Scallywag Distilling.
After a day of tastings, you will want somewhere comfortable to land. Among hotels near Mercer, PA, Tara – A Country Inn in Clark offers the charm of a country inn with full-service comfort, plus the advantage of sitting right next to Dock Side Cellars. Guests can unwind with dinner at Ashley’s Fine Dining Room, grab a drink at Stonewall’s Tavern, or stop by Vivien’s, the poolside eatery, for lunch. It turns a one-day trail visit into a full weekend away without another long drive home.
What is the Mercer County Wine and Brew Trail?
It is a driving trail connecting wineries, breweries, cideries, and distilleries across Mercer County, Pennsylvania, split into the Northern Lake Trail and the Southern Amish Countryside Trail.
What is a wine trail?
A wine trail is a mapped route connecting several wineries, and often breweries or distilleries, in one region, designed so visitors can plan a multi-stop tasting day without long drives between stops.
What are the best things to do in Mercer County, PA?
Beyond the wine and brew trail, Mercer County offers shopping in Volant and New Wilmington, Grove City Premium Outlets, and access to Pymatuning State Park.
A San Juan Island winery tasting is one of the best ways to spend a slower day on the island, especially when you pair it with a stop at a craft brewery and a small-batch distillery. San Juan Island has built a genuinely local food and drink scene, and a single day gives you enough time to sample wine, beer, and spirits without ever feeling rushed. Add a lunch stop for fresh oysters and a scenic drive between tasting rooms, and you have the makings of a proper weekend getaway.
For guests staying at Tucker House Inn or Harrison House Suites, this itinerary works especially well because everything sits within a short drive of Friday Harbor. Start at the island’s original winery, swing by a working shellfish farm for lunch, sample the tap list at the local brewery, and finish with spirits at the distillery. None of it needs to be rushed. Just designate a driver, since this is a tasting day, and leave room to pull over if you spot a farm stand or a view worth stopping for.
San Juan Vineyards is the island’s first and oldest commercial winery, planted on a former sheep farm in the northern part of the island. The wine list draws from grapes grown both on San Juan Island and in Washington’s Columbia Valley, so a tasting here gives you a real sense of Pacific Northwest wine alongside something distinct to the island itself. Plan on an hour in the tasting room, ask about the winemaking process, and enjoy the property before moving on to your next stop.
Building a wine and beer tasting day into a full weekend getaway is easy when you are staying in Friday Harbor. You can spend the day working your way through tasting rooms, then come back to a comfortable room or suite each evening instead of packing everyone into a single afternoon. It also puts you close to the shops in Friday Harbor and the harbor waterfront if you want a slower morning before you start.
After the winery, head to Westcott Bay Shellfish Co. for lunch. The working oyster farm sits about 20 minutes from Friday Harbor, and you can eat right beside the tidelands where the shellfish are raised. Oysters and wine pair naturally, and this stop gives you one of the more distinctive food experiences on the island.
Head back toward Friday Harbor for San Juan Island Brewing Co., where the beer is brewed on site and the tap list rotates through everything from lighter styles to hop-forward ales. If you cannot decide what to order, ask for a flight so you can compare a few side by side. The brewery also runs a full food menu, so it works as a happy hour stop or a heavier afternoon meal depending on how the rest of your day is shaping up.
Close out the day at San Juan Island Distillery, where small-batch spirits are made using local ingredients and Pacific Northwest influences. Take your time here. A distillery tasting is as much about hearing how the spirits are produced as it is about finding a new favorite to take home. Tasting room hours can shift seasonally, so check the distillery’s current schedule before you go.
Book your stay first, then build the rest of your San Juan Island winery day around it. Book your Friday Harbor bed and breakfast at Tucker House Inn or Harrison House Suites and come back each evening to a quiet room just blocks from downtown. For a full food and drink weekend, add dinner at our own Coho Restaurant before turning in.
Is San Juan Island worth visiting for a wine and beer tasting day?
Yes. San Juan Island has a working winery, a craft brewery, a small-batch distillery, and a shellfish farm all within a short drive of Friday Harbor, which makes a full tasting day easy to plan without long drives between stops.
What is San Juan Island Brewing Co. known for?
San Juan Island Brewing Co. brews its beer on site in Friday Harbor and rotates through a tap list that ranges from lighter, crisp styles to hop-forward ales and darker beers, along with a full food menu.
How long is the ferry ride to San Juan Island?
Ferry times vary by departure point and route, so check the current Washington State Ferries schedule before your trip. Staying overnight in Friday Harbor means you are not racing the ferry schedule to fit in a full tasting day.
What else is there to do on San Juan Island besides wine tasting?
Beyond wineries, breweries, and the distillery, San Juan Island offers hiking trails, scenic parks, whale watching, kayaking, and the shops of downtown Friday Harbor, all of which pair well with a slower weekend getaway.
Mount Hope Estate stands out as one of the most distinctive destinations in eastern Pennsylvania, offering a blend of history, entertainment, and craft beverage experiences. Located in Lancaster County, the estate is widely recognized for its immersive events, including the Pennsylvania Renaissance Faire, as well as year-round festivals and tastings at Mount Hope Estate & Winery. Visitors often arrive expecting a single attraction and quickly realize the property offers an entire day, or even a full weekend, of activities.
The estate’s history dates back more than 200 years, when it served as the home and operational center for the Grubb iron dynasty. Today, the preserved Federal-style mansion and surrounding grounds provide a glimpse into early American industry and architecture. The formal gardens, inspired by traditional English designs, remain one of the most notable features, offering a structured landscape that reflects the estate’s early 19th-century origins.
Mount Hope Estate events are a major draw throughout the year. The Pennsylvania Renaissance Faire transforms the grounds into a lively 16th-century village, complete with costumed performers, artisan vendors, and jousting tournaments. Additional events, including the Celtic Fling and themed dinner theater experiences, ensure there is always something new to experience. Guests can also enjoy tastings at Mount Hope Winery, Swashbuckler Brewing Company, and other on-site producers, making it easy to explore local flavors in one location. It’s just one of the best things to do in PA!
Extending your visit allows for a more relaxed experience. The South Mountain Inn is an incredible Bed and Breakfast in Pennsylvania that complements a day at Mount Hope Estate. The property nearby offers a quiet retreat with views of the surrounding countryside. It also has a reputation for being one of the most romantic wedding venues near Philadelphia!
Guests can return from a day of exploring to thoughtful amenities, including afternoon refreshments, comfortable accommodations, and a peaceful atmosphere. Its proximity to Mount Hope Estate and other attractions near Reading, PA, makes it a convenient and well-rounded place to stay.
With its combination of historic significance, engaging events, and local food and drink, Mount Hope Estate remains one of the most unique attractions in Pennsylvania. Whether visiting for a festival or a weekend getaway, it offers an experience that continues to draw visitors year after year.
Massbach Ridge Winery offers one of the most enjoyable wine tasting experiences in northwest Illinois, making it a popular stop for couples exploring Galena wineries. With both a scenic vineyard near Elizabeth and a convenient tasting room in downtown Galena, visitors can experience local wines in two unique settings during a single getaway.
Located about 20 miles from Galena, the vineyard provides a countryside setting where guests can sample estate-grown wines while overlooking rolling vineyards and rural landscapes. Outdoor seating areas invite visitors to relax with a glass of wine and enjoy the slower pace of the region. Since opening in 2003, Massbach Ridge Winery has expanded from a small vineyard into one of the area’s best-known wineries, producing more than 20 varieties of wine. Favorites such as Massbach Stomp, Sunset Rosé, and Vignoles continue to attract visitors seeking an authentic Galena wine tasting experience.
Guests can enjoy guided tastings, casual wine flights, vineyard walks, and seasonal events throughout the year. Live music performances, grape harvest celebrations, and the annual grape stomp provide additional opportunities to experience the winery beyond a traditional tasting. Guided tours also offer insight into the winemaking process while showcasing the vineyard’s history and growth.
For visitors planning a couples getaway, Jail Hill Inn provides an exceptional home base near both Massbach Ridge Winery and downtown Galena. Located inside the historic former Jo Daviess County Jail, this luxury Galena bed and breakfast combines historic architecture with modern comfort and personalized hospitality.
Guests enjoy spacious suites featuring king-sized beds, premium linens, and thoughtfully appointed accommodations. Each morning begins with a three-course breakfast prepared from scratch using locally sourced ingredients. In the afternoon, guests can enjoy a wine and cheese reception featuring charcuterie, artisan cheeses, fresh fruit, homemade cookies, and a bottle of wine delivered directly to their room.
The downtown Massbach Winery tasting room is just a short walk from Jail Hill Inn, allowing guests to continue their Galena wine tasting experience without leaving town. Combined with nearby restaurants, shopping, historic attractions, and scenic drives, Massbach Ridge Winery remains one of the best things to do in Galena for couples seeking a memorable Midwest getaway. Book your stay at Jail Hill Inn and experience the best of Galena wine country.
If you’re planning a luxury getaway to the Finger Lakes, Fox Run Vineyards deserves a place at the top of your itinerary. Located along the western shore of Seneca Lake, this respected estate winery has been producing exceptional wines since 1984 and remains one of the most celebrated stops among the best Finger Lakes Wineries.
Known for its estate-grown Rieslings, Pinot Noir, and carefully crafted tasting experiences, Fox Run Winery combines scenic lake views with a thoughtful approach to sustainable farming and hospitality. Guests arriving at the property are welcomed by a striking handcrafted iron gate before stepping into one of the region’s most inviting tasting rooms.
Wine tasting at Fox Run Vineyards goes far beyond the standard flight. Rotating selections often include limited-release varietals and aged vintages, giving returning visitors something new to discover throughout the year. Guests can also enhance their tasting with curated cheese, charcuterie, or chocolate pairings designed to complement each pour.
Guided walking tours provide an inside look at the vines, soil, and sustainable farming practices that shape every bottle. The winery’s café serves locally sourced, fresh seasonal dishes with lakeview seating.
As one of the most popular destinations on the Seneca Lake Wine Trail, Fox Run Vineyards pairs perfectly with nearby wineries like Hermann J. Wiemer Vineyard, Lamoreaux Landing Wine Cellars, Three Brothers Wineries and Estates, and Lakewood Vineyards. Together, they create a memorable wine country itinerary filled with exceptional tastings at the best Finger Lakes wineries.
After a day exploring Seneca Lake Wineries, returning to a luxury Finger Lakes Wine Country Hotel makes the experience even more rewarding. The Inn at Gothic Eves in Trumansburg offers beautifully appointed guest rooms, personalized hospitality, an on-site spa, and farm-to-table breakfasts crafted with local ingredients. With its convenient location near the Seneca Lake Wine Trail, the Inn provides an elevated retreat for couples, wine enthusiasts, and anyone planning a luxury Finger Lakes escape. Book your stay and experience the best of Finger Lakes Wine Country for yourself.
Winter brings a refined feeling to Virginia wine country, and Veritas Winery stands out as a memorable stop during the season. Located in Afton just outside Charlottesville, Veritas Winery is a defining destination along the Monticello Wine Trail, known for expressive wines, polished hospitality, and vineyard views that feel especially inviting in winter.
Wine tastings at Veritas Winery are thoughtfully curated, offering guests a chance to explore classic varietals crafted with balance and skill. The quieter winter months allow for a more personal tasting experience, where the focus stays on the wines and the story behind them. With European influence and a strong connection to Virginia terroir, each pour reflects the intention behind the estate’s winemaking philosophy.
Veritas Winery is also an ideal starting point for discovering more of the Monticello Trail. Nearby wineries such as Afton Mountain Vineyards, Lovingston Winery, Pippin Hill Farm and Vineyards, Mountain and Vine Vineyards, and Flying Fox Winery showcase the diversity of Virginia wineries. Each stop offers its own approach to winemaking, tasting styles, and hospitality, making winter an excellent season to explore.
A winter wine getaway is elevated when lodging becomes part of the experience. Choosing a nearby Virginia winery bed and breakfast offers guests comfort, elevated design, and welcoming hospitality after a day of tasting. At The Orchard House B&B, spacious guest rooms, shared gathering areas, and beautifully maintained grounds create a setting that encourages guests to relax and enjoy the season.
Each morning begins with a multi-course breakfast featuring farm-fresh ingredients, quality coffee, and house-made favorites, a perfect way to prepare for another day along the Monticello Trail. Guests can also explore the on-site vineyard, featuring Manseng and Petite Verdot vines, with seasonal tastings and bottles available for purchase.
Winter is an ideal time to experience Veritas Winery and Virginia wine country with fewer crowds, thoughtful tastings, and a stay that feels both indulgent and comfortable. Plan your winter getaway today.
If you are staying in Baraboo and someone tells you to save an afternoon for wine tasting, it’s Wollersheim Winery they mean. Sitting about 20 minutes south along the Wisconsin River in Prairie du Sac, it’s the perfect wine stop away from the Dells and Devil’s Lake crowds. Between the tasting room, distillery, and bistro, Wollersheim has grown into one of the most recognizable names among Wisconsin wineries, and it is a great addition to any Baraboo itinerary.
Wollersheim Winery traces back to the 1840s, when Hungarian nobleman Agoston Haraszthy first planted grapevines on the hillside before moving on to help found California’s wine industry. The Kehl family ran the property as a working winery until a hard winter in 1899 wiped out the vines. Bob and JoAnn Wollersheim bought the land in 1972 and started replanting, and winemaker Philippe Coquard, who arrived from France’s Beaujolais region in the 1980s, has led the winery since. The property now holds a place on the National Register of Historic Places, and the original hillside wine cave has been restored into a small exhibit on the estate’s past.
Wollersheim Winery is really three experiences in one. The winery itself pours Prairie Fumé, a dry white made from a French American hybrid grape, alongside a rotating lineup of reds and dessert wines. The distillery, added in 2015, produces brandy and gin. The bistro serves a scratch-made menu designed to pair with their wines. Tours and tastings run throughout the day, though hours shift seasonally, so it is worth checking Wollersheim’s site before you drive down. Prairie du Sac sits close to Sauk City as well, so it’s easy to make a stop in either town.
Wollersheim Winery makes an easy half day trip from Baraboo. Start your day with a morning hike at Devil’s Lake or a stop in downtown Sauk City on the way south. Wine tasting in Wisconsin has few stops with this much history behind the label, and Wollersheim remains the benchmark for the region.
You might be wondering: where can you stay near Wollersheim Winery that is not a highway motel? Ringling House Bed and Breakfast sits in downtown Baraboo, about 20 minutes north of the winery, and is one of the better options among Hotels near Wollersheim Winery for a wine weekend. Built in 1901 for Charles Ringling of circus fame and listed on the National Register of Historic Places, the house puts you within walking distance of Baraboo’s restaurants while keeping you close to Prairie du Sac, Circus World, and Devil’s Lake State Park. Book your stay, spend the afternoon tasting wine, and come back to a historic house with a home cooked breakfast waiting the next morning.
Frequently Asked Questions
Where is Wollersheim Winery located?
Wollersheim Winery sits in Prairie du Sac, Wisconsin, on a hillside overlooking the Wisconsin River, close to Sauk City.
How far is Wollersheim Winery from Baraboo?
It is about 16 miles, roughly a 20 to 25 minute drive south from Baraboo via Highway 12.
Does Wollersheim Winery have food?
Yes. The on-site bistro serves a seasonal menu built to pair with the winery’s wines.
Where should I stay near Wollersheim Winery?
Ringling House Bed and Breakfast in downtown Baraboo is about 20 minutes from the winery and puts you within walking distance of Baraboo’s own restaurants and shops.
What is Wollersheim Winery known for?
Wollersheim is best known for Prairie Fumé, its flagship dry white wine, and for being one of the oldest wineries in Wisconsin, with roots dating to the 1840s.