Top Virginia Holidays in 2026

Ole Crow Tours warmly invites you to explore the very best that Virginia’s renowned wine region has to offer in comfort and style. Simply sit back, relax, and let us handle all the details, carefully ensuring a seamless and unforgettable experience for you and your guests to truly savor every moment. On this thoughtfully curated tour, you’ll be enjoying visits to 3 carefully selected wineries located on the scenic eastside of Charlottesville. This journey will take us through the charming Keswick area, once home to Thomas Jefferson’s old stomping grounds, a region rich with history, natural beauty, and timeless elegance.

Be transported back to Williamsburg in 1943 in this 1-hour character tour. Learn how the citizens of the town are dealing with rationing, blackout drills, and all the new servicemen in town during the Holiday season. Please note that each tour is unique, so the advertised routes may vary. You will be guided through town by either a USO Hostess or an Air Raid Warden. However, for evening tours, the guide will solely be an Air Raid Warden. Routes may also be changed to accommodate activities in Colonial Williamsburg. Shades of Our Past is not affiliated with Colonial Williamsburg; therefore, this tour does not include entrance or admission into Colonial Williamsburg-owned buildings. Since the tour is through the streets of Colonial Williamsburg it is weather contingent. Please be prepared for all weather conditions. Please be aware that due to staff participation in other events, tours may be unavailable on certain days. For details about these programs, please visit our website.

Your tours are intentionally designed for small groups, allowing us to provide a level of service and attention that larger tour operators simply cannot match. We take the time to understand your preferences, recommend venues that fit your group's personality, and create an itinerary tailored to your occasion. Whether you're celebrating a birthday, anniversary, bachelorette party, date day, or simply enjoying time with friends, every experience is customized around you. What truly makes us different is your concierge-style approach. From the moment we pick you up until we safely return you home, we're focused on the details. We coordinate timing between venues, help keep your day running smoothly, offer local knowledge of Virginia wine country, and provide the flexibility to adjust the day as needed.

Join us for haunting tales of Richmond's Court End neighborhood on a guided walking tour. Take in a unique urban landscape where historic and modern Richmond come together in dramatic fashion, with historic homes, medical buildings, museums, and more. See the home of America's most renowned Supreme Court Chief Justice and hear about the tragic tales that have resulted in hauntings within the historic house. Learn about a grim resurrectionist who terrified the community in the 1800s and continues to frighten medical students in an architecturally stunning Egyptian building. Move through the neighborhood and learn how the regal historic structures and gleaming veneers of modern Richmond belie the tumultuous and eerie history that remains just below the surface.

With the beauty of the Blue Ridge Mountains surrounding the quaint vineyards of Virginia, this private wine excursion delivers a peaceful and harmonious experience in the great outdoors. A private chauffeur will cruise you and your guests from historic Charlottesville to the countryside. Spend the day touring the area and sampling wines from multiple wineries. On the Wine Trail, you’ll have your choice of which tasting rooms to visit and when to have a picnic lunch.

Simplification of Choices: By breaking down the variety of cheeses into six categories, you make cheese accessible to all. This simplifies the cheese aisle so you can make confident choices. Personalized Approach: Not just a simple tasting but a personalized journey, allowing you to discover your preferences and feel more connected to your choices. Educational Component: The educational aspect enriches your understanding and appreciation, making you feel like experts by the end of the session. Engagement and Fun: The playful tone and interactive format create a lively atmosphere. This isn’t just a tasting; it’s an adventure filled with laughter and community. Practical Takeaways: A straightforward guide on how to shop for cheese and pair it with wine. Memorable Experience: Combining sensory enjoyment with personal discovery and social interaction makes for a memorable event. By weaving together these elements, your experience becomes a delightful and unforgettable journey!

Build your wine confidence. No snobs here! White & Red Wine Crafting, Aeration Techniques, Rosé Revelations, Restaurant Etiquette, Molecular Pairing, Chocolate and Wine Pairing made easy!

Have you ever wondered how our modern Christmas traditions began? Join us for a 1-hour walking tour through the streets of Colonial Williamsburg, where your guide will reveal the colonial Christmas celebrations that shaped our current traditions. You'll also learn how the decorating style of Colonial Williamsburg influenced decorations across the nation. Shades of Our Past is not affiliated with Colonial Williamsburg; therefore, this tour does not include entry to any buildings owned by Colonial Williamsburg. The tour takes place through the streets of Colonial Williamsburg and is subject to weather conditions. Please be prepared for various weather scenarios. Additionally, the advertised tour route may change based on activities in the Historic Area. Please note that tours may be unavailable on certain days due to staff participating in other events. For more details about these programs, please visit our website.

Experience one of Virginia Beach’s most unique activities aboard Chesapeake Bay Pedal Club’s BYOB pedal party boat. Cruise through the scenic Rudee Inlet with your favorite drinks, music, and friends while our licensed captain handles the navigation. Pedaling is completely optional—you can help power the boat or simply relax and enjoy the ride. (we have an engine folks). With seating for up to 20 guests and an onboard restroom, it’s the perfect outing for birthdays, bachelor and bachelorette parties, family gatherings, date nights, and visitors looking for a fun day on the water.

An evening of chilling tales and lively atmosphere awaits on the Williamsburg Ghost and Taverns Pub Crawl. This unique adventure combines the thrill of ghost stories with visits to historic taverns, creating a memorable night out in Williamsburg. With your ticket, enjoy a complimentary first drink while immersing yourself in the local history and spooky legends. Perfect for those seeking a blend of fun and fright in a vibrant social setting, this pub crawl is an ideal choice for friends and enthusiasts of the supernatural alike. Join us for an unforgettable night filled with laughter, chills, and camaraderie.

Discover Virginia’s Monticello Wine Trail on a private winery tour in Charlottesville. Create an itinerary with your dedicated guide based on your group’s wine interests and travel in a comfortable, air-conditioned vehicle to each destination. Enjoy guided tours of each vineyard, play indoor games, and savor included snacks during the tour. Purchase wine tastings, if you’d like.

Immerse yourself in the excitement of Richmond, Virginia’s thriving craft beer scene—and learn all about beer styles and the brewing process from your guide—on this private, half-day tour. Meet your guide in central Richmond for a tutored tasting before setting off in your comfortable, air-conditioned minibus. You’ll visit three highlight breweries, will enjoy generous tastings at each, and will go behind-the-scenes at one to learn more about the brewing process.

Culinary Experience: Join Winemaker Donna for a Guided Lunch Featuring: Five categories of wine Tapas-sized food pairings Three delicious entrees A cheese course with three exquisite cheeses Three delightful desserts Three decadent chocolate delicacies Highlights: Learn how to achieve perfect pairings every time Discover the nuances of wine Experience enlightening 'aha' moments for social gatherings Come hungry for a deliciously educational meal!

Dive into adventure with Let’s Roam, your go-to for the ultimate app-led adventure hunts! Step into a world where every landmark and hidden gem is waiting to be discovered. Challenge yourself with trivia, tackle brain-teasing puzzles, and embark on an epic journey of exploration! Whether you’re collaborating with your crew or turning up the competition, Let’s Roam Adventure Hunts guarantee a blast for all. Perfect for any occasion—whether it’s a spontaneous outing, a wild bachelorette bash, a festive birthday celebration, or a team-building extravaganza. Each player gets to dive into an interactive role, ensuring every challenge is as thrilling and unique as the next. So, gather your squad, choose your adventure, and let the good times roll! With Let’s Roam, every outing becomes a treasure trove of memories and excitement. Are you ready to conquer the city and create unforgettable experiences? Let’s Roam and make every day an adventure!

Experience the top-rated brewery and meadery tour in Richmond, where you'll explore the city's best craft alcohol hotspots while enjoying tours and tastings included in your ticket! Operating year-round, this immersive experience takes you through Scott’s Addition, home to some of the region’s finest breweries, cideries, and meaderies. Led by expert guides, this USMC Disabled Combat-Veteran-Owned, women and minority-led tour brings you to Buskey Cider, Strangeways Brewing, Ardent Craft Ales, Black Heath Meadery, and Blue Bee Cider. At each stop, you’ll sample exceptional craft beverages while learning about the production process and the rich history behind each establishment. Whether you're a beer connoisseur, cider lover, or mead enthusiast, this tour is the perfect way to drink, learn, and explore the city. Perfect for private groups, bachelorette parties, and special events, this unique bar crawl lets you experience Richmond’s thriving craft scene like never before!

Avoid the crowds of a traditional pub crawl and head out on a fun scavenger hunt with this app-based experience, which takes you to some of Alexandria's best watering holes. You and your group of friends, family members, or colleagues spend the evening completing challenges and solving problems while visiting fun pubs and bars along the way.

Discover Virginia Wine Country the way it was meant to be experienced—privately, comfortably, and entirely on your schedule. Skip the crowded buses and cookie-cutter itineraries. This fully private experience is designed exclusively for your group, allowing you to explore Charlottesville's renowned wineries, breweries, cideries, and distilleries at your own pace while traveling in a luxury Chevrolet Suburban featuring a panoramic sunroof. Whether you're celebrating a special occasion, planning a romantic getaway, reconnecting with friends, or simply looking to experience the best of Virginia wine country, our local concierge team helps create a seamless day from start to finish. 100% Private Tour — No strangers, no shared transportation, no fixed schedule. Customized Itinerary — Visit the wineries, breweries, cideries, & tasting rooms that match your group's preferences. Local Expertise — Our team knows the region's hidden gems, iconic vineyards, and reservation-only experiences.

Enjoy a night of drinking and ghost stories as you explore Williamsburg with the help of a tour guide to show you around. Stop at a range of local establishments for drinks and pass by historical sights on the way while you listen to the macabre tales told by your engaging tour leader. Make sure you come thirsty for some drinks and hungry for some thoroughly researched spooky stories.