Popular Weekend Events in Virginia (May Updated)

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Popularity New Arrivals

Gathering in the Gap Music Festival - 2026 | Southwest Virginia Museum Historical State Park

May 23, 2026 (UTC-4)

Big Stone Gap

Concerts

An immersive festival that preserves and perpetuates authentic, traditional, and historical music and folk arts of Southwest Virginia. Memorial Day weekend is the perfect time to wander the park grounds, browse fine regional crafts, and enjoy some delicious food while listening to premier performers. In addition to the evening entertainment, there will be several other opportunities throughout the day to enjoy the musical traditions of the region. The Acoustic Arbor, Competition and Gathering Place stages will have performances all afternoon by a variety of musicians and songwriters, and are free and open to the public. Sponsored by the Town of Big Stone Gap, the Gathering Place Beer and Wine Garden offers spirits from local wineries, breweries and/or cideries. Other activities available as part of the Festival: Gathering in the Gap boasts a variety of activities for children, such as crafts and games, as well as the "Pint-Sized Pickers" tent, sponsored by Mountain Empire Community College. The Museum will be open from 10am-5pm and will feature the annual "A Stitch in Time" Quilt Exhibition. Various programming such as tours of the Interstate 101 Railcar and the historic Poplar Hill neighborhood. Schedule TBA. Craft and Artisan Vendors, Demonstrators, and Food Vendors will be open from 11am-7pm. NEW THIS YEAR - the Johnny Cubine Camp & Carve will be offered as part of the Gathering in the Gap Music Festival. This will be held at the nearby Jessie Lea RV Park and Campground. Shuttle Info: A free shuttle will be available to transport guests from the parking area at Bullitt Park to the main festival site (the grounds of the Southwest Virginia Museum Historical State Park) as well as to the Camp & Carve site. This will be available on Saturday ONLY and will begin at 10am. Click here for the official Gathering in the Gap website. Information Source: Friends of the Southwest Virginia Museum | eventbrite

The Faerie Faire | 1209 Craft Ln

May 30, 2026 (UTC-4)

Virginia Beach

Cultural Experiences

Information Source: Curators Keys | eventbrite

Spring Forest Family Day with Pete Moss | Macaulay Heritage Park (Stone Room at the back of Macaulay House)

May 30, 2026 (UTC-4)

Prince Edward County

Family Events

Information Source: Wildhearts: A Prince Edward County Forest School | eventbrite

Picton ComiCon : June 28th 2026 : Comic Con | Prince Edward Curling Club

Jun 28, 2026 (UTC-4)

Prince Edward County

Arts

Information Source: Pop Culture Canada | eventbrite

Charlottesville | Madison Cunningham《The Ace》Tour | The Jefferson Theater

Sep 19, 2026 (UTC-5)

Charlottesville

Concerts

HISTORIC HAUNTS OF STAUNTON -- SPRING TOURS | CITY PARKING GARAGE BESIDE THE FORMER STONEWALL JACKSON HOTEL

May 16, 2026 (UTC-4)

Staunton

Celebration

Staunton's history and haunts all rolled into one fun, creepy tour .. HISTORIC HAUNTS OF STAUNTON—where the past refuses to rest. Step into the shadows of downtown Staunton, Virginia, on our most popular and longest-running ghost tour. For 90 chilling minutes, guided only by lantern light, you’ll walk the same streets where spirits still linger, trapped between time and terror. From the restless soul of Mary Baldwin to the ghostly echoes of James Vames and Jimmy Atkins, these figures shaped Staunton’s history—and in death, they refuse to leave. What keeps them tethered to this world? What secrets do they whisper in the dark? Discover why Staunton is a true paranormal hotspot, pulsing with unexplained activity. Hear the eerie stories, feel the presence of the beyond, and witness firsthand why some say the dead outnumber the living in the Queen City. Dare to walk with us? Tour meets/begins from the corner of Johnson and New Streets (City Parking Garage across from Mill Street Grill Restaurant) by the stoplight. Parking in the garage is FREE. Please call 540-448-2743 for more information. Information Source: Ghosts of Staunton Walking Ghost Tours | eventbrite

Graduation Weekend | 8:00PM SEATING | The Birdcage

May 16, 2026 (UTC-5)

Charlottesville

Family Events

Information Source: The Local Catering | eventbrite

Graduation Weekend | 5:30PM SEATING | The Birdcage

May 16, 2026 (UTC-5)

Charlottesville

Family Events

Information Source: The Local Catering | eventbrite

From Debt To Destiny - Personal Finance Conference | Stacy C. Sherwood Community Center

May 16, 2026 (UTC-4)

West Fairfax

Cultural Experiences

Stop guessing with money. Learn how to eliminate debt, reclaim cash flow, and prepare to pay off your home faster, the right way. An empowering 3-hour event designed to help individuals reclaim cash flow, raise their credit scores, and build generational wealth through biblical principles and financial wisdom . WHAT YOU WILL LEARN AT THE “ FROM DEBT TO DESTINY ” CONFERENCE How to stop the financial bleeding Why most people stay stuck in debt, even with a good income The foundational principles required before using advanced strategies How to eliminate credit card debt strategically How to reclaim cash flow and create momentum What velocity banking is, and is not How to responsibly prepare to pay off your home in 7 years or less -------------- Attire: Business Casual | Evening Blessings & Bites (Meal) – Catered TICKET IS NON-REFUNDABLE BUT TRANSFERRABLE | Contact Host: pearlavise.va@gmail.com Information Source: eventbrite

Neptune's 21st Annual Spring Wine Festival | Neptune's Park

May 16, 2026 (UTC-4)

Virginia Beach

Cultural Experiences

Travel the world without leaving the beach...enjoy 70+ wines from 8 countries, live music, food trucks, AND zero-proof options! Travel the world without leaving the beach! 31st Street Park is transformed into a hub of tasting stations from around the world with over 70 wines from 8 countries, each featuring blends and styles that are sure to ignite the traveler in you. Zero Proof Options – are you interested in non-alcoholic wine and seltzers? We have fun new offerings just for you! TICKETS: FROM $40 Each tasting ticket includes a commemorative wine glass and tastings throughout the event. You must purchase a ticket to enter the event. Purchase a ticket and receive a $5 off promo code for Neptune's Coastal Craft Beer Festival and Neptune's Fall Wine Festival! Promo code will be emailed with your ticket confirmation. Tier 1, through March 14: $40 Tier 2, through May 9: $45 Tier 3, beginning May 10 unil sold out: $50 TABLES: $450 Each reserved table includes 8 event tickets, a reserved table with chairs, plant centerpiece to take home, PLUS an ice bucket filled with a bottle of wine and 8 bottles of water! FOOD TRUCKS: TBA TBA LIVE MUSIC: TBA TBA IMPORTANT EVENT INFORMATION: Event will be held Rain or Shine. Tickets are required for entry into this event. No refunds will be issued. MUST BE AGE 21+ TO ATTEND THIS EVENT. No one under the age of 21 (including children in carriers or strollers)will be permitted into the event. Photo ID will be checked for proof of age. No pets or emotional support animals are permitted; however, in accordance with the Americans with Disabilities Act, service animals are permitted. No wagons, beach carts, or wheeled coolers will be permitted. Small bags and shoulder-strapped coolers are permitted. No personal tables or large/patio style umbrellas permitted. Personal rain umbrellas are permitted. No personal speakers permitted No weapons permitted Outside food and non-alcoholic beverages are permitted. All bags/coolers will be inspected at the gate. Chairs and blankets are permitted. Food Truck offerings subject to change. Information Source: Virginia Beach Neptune Festival | eventbrite