Top Virginia Seasonal & Special Occasions - page 2

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.

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.

Experience Colonial Williamsburg’s holiday traditions with the added insight of a costumed guide who brings local history to life. Instead of exploring on your own, discover the stories behind the town’s seasonal decorations and celebrations while strolling its historic streets. It’s an engaging way to see how Christmas has been celebrated through the centuries.

Take the stress out of your family excursion in Charlottesville with this private round-trip transfer from Pantops Shopping Center to the destination of your choice. Skip the guesswork of ride-sharing services or taxis and schedule your pickup in advance, then head straight to your excursion location—including wineries, sights, parks, concerts, or other destinations. Enjoy a few hours of free time to enjoy your family activity before the return trip to the pick-up location or other drop-off point.

Richmond, Virginia is celebrated for its over-the-top holiday lights displays every year—and this tour makes exploring them simple. In the evening, depart from Williamsburg via climate-controlled vehicle and travel to Richmond. You’ll learn all about the city’s history of tacky lights displays, will admire some of the best examples, and will even see the Christmas tree in front of the Virginia State Capitol.

Turn a day in Virginia wine country into a seamless experience. Our private wine & beer tours are designed for couples, small groups and anyone looking to enjoy the best of the Monticello Wine Trail without worrying about driving, planning or logistics. Whether you're celebrating a birthday, planning a girls day, or just want a relaxing afternoon, we make it effortless from start to finish. Your experience includes: 6 hours Private, luxury vehicle Custom itinerary or let us plan it for you Door-to-door pickup and drop-off Flexible timing & personalized experience

We would like to personally invite you to join us on an unforgettable journey through the beautiful countryside of Charlottesville and the surrounding area. As you enjoy tastings of some of Virginia's finest and most celebrated wines, you will be completely immersed in the rich history shaped by Thomas Jefferson’s lasting influence on the region. This experience promises to be both relaxing and enlightening, blending the natural beauty, exquisite flavors, and historical depth unique to this area.

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.

Come on to our Haunted Pub Crawl Tour presented by US Ghost Adventures! Many of the best clubs and pubs in the area are housed in the historic structures that dot the Shockoe Bottom neighborhood of Richmond. This trip is created to give you a taste of the best Richmond has to offer, like Farmhouse hard cider, as well as a window into the afterlife of some of its people, such as the four ghosts rumored to haunt St. John's Church.

What could be better than Christmas in Alexandria? On this six block, hour long walking tour, enjoy the festive decorations of this beautiful town while listening to a seasonal blend of Alexandria Holiday History and forgotten Christmas folklore. We're also bringing back the Victorian tradition of 'scary ghost stories by the fire', as your costumed guide ends the tour with haunted tales by lantern light in a historic graveyard. Don't miss this limited time only, seasonal event! Tours Run on the following dates: November 26, 28, & 29 at 8:00pm December 5, 13, & 20 at 8:00pm December 6, 14, & 21 at 7:30pm December 26 - January 1 at 7:00pm

Experience the magic of Colonial Williamsburg Christmas on one of our most popular private walking tours. Discover the beauty of Colonial Williamsburg's Christmastide as we stroll from the Williamsburg Inn along Duke of Gloucester Street, admiring spectacular holiday decorations, historic homes, and 18th-century architecture. Learn how handcrafted wreaths and garlands are created from fresh greenery, fruits, seed pods, oyster shells, feathers, and other natural materials, then judged in the Professional, Amateur, Trades, and Crafts divisions. Your knowledgeable local guide brings history to life with stories of Christmastide traditions celebrated by plantation owners, middling families, and military during the Revolutionary War. It's the perfect way to experience Christmas in Colonial Williamsburg, Virginia. Note: Traditional ginger cake is included. Tours before 7PM include a beverage. Grand Illuminations: first three Saturdays in December. Yule Log ceremonies: first three Fridays.

Engage in a relaxed evening at Speak Easy at The Colonies of Williamsburg, where good vibes and meaningful conversations flow freely. This event invites you to connect with others in an informal setting, making it perfect for sharing stories and enjoying delightful company. Whether you’re looking to unwind or meet new friends, this gathering offers an approachable atmosphere to explore and enjoy. Don’t miss this chance to participate in a unique social experience at a historic location.

The Ghost Tour is Williamsburg's first and only murder-focused tour. Explore areas that other history tours would be afraid to visit. Explore a historic city that conceals a sinister and unsettling past. A netherworld of horrific death and hatred. Accompany your guide on foot to some of our favorite local watering establishments. To help you get ready for what's to come, try a drink with a murder theme or one of the pub's specialty beverages. Then, take a stroll through the dim, peaceful streets of Historic Williamsburg, where you may learn the real stories of the city's most notorious crimes. There's nothing ghostly about Williamsburg's scariest tour. It has to do with murder.

Celebrate the magic of the season this year with Holly Jolly Hunt. Holly Jolly Hunt is an app based scavenger hunt that you can play anywhere of your choosing. Explore the city and look for holiday related items, both traditional and not so traditional. Take a photo through the app to score points for your scavenger hunt team. Perform fun, holiday challenges that will bring laughter to your team. See your score on the leaderboard compared to other teams from all over. Holly Jolly Hunt is guaranteed to provide lasting holiday memories. Whether you play with friends, family, or even co-workers, Holly Jolly will put a smile on your face for the rest of the year!

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.

The Double Decker Party Pontoon turns golden hour into an event. With two decks, a water slide, and room for up to 14 people, your group can spread out, take in the view, and squeeze in a little more fun before the sun sets over Wallops Island. Sea Rocket keeps the slide running with an onboard water pump so the good times last right up until sunset. Gather your group, bring a little something to sip on, and end your day in Chincoteague the way it deserves to end, out on the water.

Celebrate the magic of the season this year with Holly Jolly Hunt. Holly Jolly Hunt is an app based scavenger hunt that you can play anywhere of your choosing. Explore the city and look for holiday related items, both traditional and not so traditional. Take a photo through the app to score points for your scavenger hunt team. Perform fun, holiday challenges that will bring laughter to your team. See your score on the leaderboard compared to other teams from all over. Holly Jolly Hunt is guaranteed to provide lasting holiday memories. Whether you play with friends, family, or even co-workers, Holly Jolly will put a smile on your face for the rest of the year!

The Holly Jolly Hunt offers a unique blend of affordability and engaging holiday activity, making it ideal for groups. Tickets are sold per team (up to 10 people), providing great value for families and friends. The hunt is self-guided and playable in any city decked out for the holidays, putting you in control of the schedule. The core of the game is its focus on fun and laughter, achieved by mixing the search for holiday items with silly photo missions and collaborative challenges. This combination ensures that the focus remains on group bonding and light-hearted, memorable competition to top the scoreboard.

Beneath the opulent veneers of Richmond's gilded age architecture and the day-to-day life of academia, bubble tales of chilling haunts, macabre murders, and bizarre paranormal activity. Join us for a spooky stroll around the Monroe Park campus as we explore stories that are often left out of your typical college brochures. Cloaked in the shadows of the beautiful and historic neighborhood, this tour includes the following spirited tales: The grim history of Monroe Park that lies hidden under the well-tended landscape of today, a hospital-turned-student dorm that still houses the spirits of long-departed patients, the ghosts of a landmark theater, and more... Your Guide will share with you the history of the neighborhood, and how it relates to the tales of the mysterious and tragic things that have led to numerous reports of paranormal activity along the tour route.

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.

Discover why Staunton’s #1 ghost tour is one of the town’s most unforgettable nighttime experiences. Operating nightly, year-round, this outdoor walking tour is led by local guides who know Staunton’s history, legends, and haunted past firsthand. As you wander the historic streets, you'll hear chilling stories inspired by documented events, local folklore, and unexplained encounters. Along the route, you'll learn the haunted history behind iconic sites including Clocktower Eats and Sweets, the SunTrust Bank Building, and Mary Baldwin University, where tales of ghostly sightings, tragic events, and mysterious happenings have become part of the town’s history. Though the tour remains outdoors, each stop offers an eerie glimpse into Staunton’s past. Perfect for private groups, bachelorette parties, birthdays, and special events, this ghost tour blends authentic history, captivating storytelling, and mystery into an unforgettable evening beneath the shadows of Staunton.

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.

The Double Decker Party Pontoon is the ultimate way to get the whole crew out on the water together. With two decks, a water slide, and room for up to 14 people, there's space for everyone to swim, relax, and soak up the sun at their own pace. Sea Rocket keeps the slide running the entire trip with an onboard water pump, so the fun never has to stop. Gather your group, bring your favorite playlist, and spend a few hours cruising Chincoteague Island on the coolest boat on the bay.

Williamsburg is celebrated as the birthplace of American liberty, but its history is not as polished as its restored streets suggest. Gallows Path explores the darker side of Colonial Williamsburg through stories of power, punishment, betrayal, confinement, and justice that did not always serve the truth. This 90-minute adults-only ghost tour, for guests ages 16+, follows historic streets after dark, connecting real colonial history with the legends and reported hauntings that followed. Your Ghost City Tours Ambassador will guide you to exterior locations tied to the Colonial Williamsburg Courthouse, Bruton Parish Church, George Wythe House, Peyton Randolph House, Public Hospital Museum, Magazine Green, and Public Gaol. This tour is not built around costumes, staged scares, or invented stories. The history is dark enough on its own. Gallows Path asks one question that grows more complicated at every stop: what happens when justice fails?