Top Virginia Holidays in 2026

You've been to winery wine tasting, but, have you been to a chocolate factory wine tasting? Welcome to our craft chocolate factory to see how chocolate is made while sipping on perfectly paired wine.

Watch the sun set over Chesapeake Bay on a 2-hour, small-group dolphin tour by kayak from Virginia Beach. Paddle along the coast as you spot Atlantic bottlenose dolphins, and see the Cape Henry Lighthouses and Chesapeake Bay Bridge Tunnel from the water.

Step back in time on a private ride through historic Fredericksburg in a fully restored 1920's Model-A. Guests meet in the heart of downtown and climb aboard cushioned seats for a 20-30min tour with open-air views and plenty of charm. Along the way you'll pass Fredericksburg's most treasured landmarks including the Mary Washington House & Monument, Huge Mercer Apothecary, Kenmore Plantation, Chatham Manor, and the Rappahannock Riverfront. Your guide shares fascinating stories of colonial times, the Civil War, and Fredericksburg's unique past while you relax and enjoy the ride. This tour is the ideal way to enjoy Fredericksburg highlights with history, nostalgia and fun all rolled into one unforgettable experience. Remember Don't Just Look at History, Ride in It!

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.

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.

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.

Join us as we discover the History of Christmas in the colony while exploring the handcrafted decorations that adorn the historic buildings. On our 1-hour leisurely stroll thru the city, you will have the opportunity to photograph some of the most iconic decorations that are uniquely Colonial Williamsburg. Handcrafted one-of-a-kind decorations made by employees and residents of the city are beautifully and proudly displayed on each building and we will discover the most beautiful and unique of this year's display. We will discover the religious, humorous, and heartfelt traditions that span the centuries. While learning how the decorations are made, how they became a tradition, and even helpful tips and tricks on how the create your own decorations at home. Christmas in Colonial Williamsburg is truly an experience that you and your family will cherish for years to come.

Take this Alexandria Boos and Booze haunted pub crawl tour and add some fun into your work week! This quick but fun tour will take you to four stops for up to two hours. This tour price does not include tastings or tours of the facilities. This tour will take you to a total of four watering holes in Alexandria, which may be a combination of craft producers in Alexandria, and local bars. There will be a variety of haunted stops in between these already notorious bars and pubs! We'll spend about 15-20 minutes to one hour at each destination. Exact lineup depends on day of week and season. Drinks are not included. The total duration is approximately 1 hour and 45 minutes. The duration of the tour includes, drinks at the establishments, history and story telling at the historic sites and walking to and from the historic sites.

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!

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. Note that dinner is not included on this tour.

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.

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.

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

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?

Richmond has rebuilt itself many times, but some stories refuse to stay buried. The Dead Don’t Forget is a 90-minute adults-only ghost walking tour through Shockoe Bottom, designed for guests ages 16 and older who want a deeper look at the city’s darker history. This tour also explores local paranormal traditions tied to Shockoe Bottom, including reports of footsteps, voices, shadowy figures, uneasy sensations, and stories that remain attached to places where the past was never fully resolved. This is an outdoor walking tour, and guests do not enter museums, stations, buildings, or tour stops. The Dead Don’t Forget is not built around cheap scares or invented legends. It uses Richmond’s real history and reported hauntings to examine what remains when a city builds over painful ground, softens uncomfortable stories, and tries to move forward without fully remembering who was left behind.

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 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.

Ale & Apparitions connects Williamsburg’s haunted history to the places where the city still gathers after dark. Beginning in Merchants Square and moving into the William & Mary nightlife district, this pub crawl blends local bars with stories of theater folklore, institutional confinement, wartime occupation, destructive fires, disturbed burials, and campus legends. It is not just a historic ghost tour with a drink stop added in — it follows the line between old Williamsburg and modern college-town nightlife, showing how the city’s past still lingers around the places people meet, drink, talk, and trade stories today. This experience blends ghost stories, colonial history, tavern culture, and a fun night out for adults. Guests will hear about the people who filled Williamsburg’s evenings, the legends that grew around its taverns, and why some believe echoes of those nights still linger. Guests must be age 21+ and bring valid government-issued photo ID.

If you want to overload your senses, this could be the one. This tour combines two of the area's top vineyards, which not only produce wonderful wine but also provide an unforgettable culinary experience. One of the stops is also recognized for its architectural design, while the other for its architectural ruins.

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.

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.

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!

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.