Food, Folks, and Fun Festivities
By Barrett Baker
Our region is home to a wide range of cultural events, from pirates running amok in the streets to festivals that celebrate diversity, freedom, expression, and unity. Many of these commemorations are filled with the joys of food, music, dancing, and educational opportunities, so visitors can absorb new experiences and leave them with a greater sense of the world. Here are a few you won’t want to miss.
Jamestown Day
When:May 9
Where:Jamestown Settlement, Williamsburg
Festivities: Marking the 415th anniversary of the establishment of Jamestown in the New World, Jamestown Day 2026 will include a several family-friendly programs, activities, and walking tours that are included in the price of admission to History Jamestown. Visitors can board a replica of the iconic Godspeed to learn how sailors navigated the seas in the 17th century, and—weather permitting—witness a demonstration of sailing maneuvers by the Discovery on the James River.
Website: jyfmuseums.org/events/programs-activities/jamestown-day
Fiestahan Filipino Market
When: May 9, 2-8 p.m.
Where: Maker’s Craft Brewery, Norfolk
Festivities: As part of LigayaFest—a Virginia-based Filipino pride festival commemorating culture, history, and food—Maker’s Craft Brewery will host a celebration of Asian American and Pacific Islander heritage month. The market will feature live music, an opportunity to shop at Filipino-owned businesses, and a variety of Filipino food trucks. Free to attend and open to the public.
Chesapeake Jubilee
When: May 14-17
Where: Chesapeake City Park
Festivities: The idea for the Chesapeake Jubilee began in 1982 when Chesapeake turned 20. This year’s event will feature rides and activities—featuring displays and exhibits from community nonprofit groups and the Armed Forces—in addition to arts and crafts vendors, music, a fireworks display, the Chesapeake 4-H livestock show and sale, as well as food and drink for all ages. The event also features the Chesapeake Kiwanis Shrimp Fest on Thursday, May 14 (separate tickets required).
Website: chesapeakejubilee.org
Bayou Bon Vivant Cajun Music, Food & Arts Festival
When: May 15-17
Where: Town Point Park, Norfolk
Festivities: This annual event evokes the culture of Louisiana. The festival features live Cajun and Zydeco music, more than 7,000 pounds of fresh crawfish—along with other Cajun treats such as gumbo, jambalaya, and beignets—in addition to an arts market that will feature crafts from vendors. There will also be reptile exhibits and other family-friendly activities.
Website: festevents.org/events/2026/bayou
Stockley Gardens Arts Festival
When: May 16-17
Where: Stockley Gardens Park, Norfolk
Festivities: Hosted by Hope House Foundation since 1984, this two-day festival features more than 125 artists from across the country and around the world using mediums that include photography, pottery, sculpture, painting, mixed media, and jewelry. One hundred percent of the proceeds from the event supports individuals with developmental disabilities.
Website: hope-house.org/events/stockley-gardens-arts-festival
Newport News Greek Festival
When: May 28-31
Where: Saints Constantine and Helen Greek Orthodox Church, Newport News
Festivities: The largest of a variety of events held throughout each year at the church, the spring edition of the Newport News Greek Festival features live cultural music and dancing, a plethora of excellent Greek foods and pastries to sample, in addition to an indoor vendor area.
Website: newportnewsgreekfestival.org
Williamsburg Greek Festival
When: June 4-7
Where: St. Demetrious Greek Orthodox Church, Williamsburg
Festivities: Enjoy home-cooked Greek cuisine, traditional Greek music and dancing, church tours, and a variety of vendors.
Website: williamsburggreekfestival.com
Blackbeard Pirate Festival
When: June 12-14
Where: Mill Point Park and Downtown Hampton
Festivities: Step back in time and enjoy swashbuckling fun as Blackbeard’s crew descends upon Hampton. Visitors will find dozens of pirates costumed in historically accurate garb, a pirate camp in Mill Point Park, and reenactments of Blackbeard’s final battle. Tall ships will be on display on the Hampton River, and visitors can enjoy a variety of children’s activities, live music, fireworks, period vendors, arts and crafts, and food trucks.
Website: hampton.gov/2008/Blackbeard-Pirate-Festival
Juneteenth Freedom Festival
When: June 13
Where: Festival Park, Atlantic Union Bank Pavilion, Portsmouth
Festivities: Juneteenth marks the day in 1865 when Union troops arrived in Galveston, Texas, to ensure the last of the enslaved African Americans were freed. The Portsmouth Freedom Festival celebrates the significance of that event with a commemoration that features live performances and music, local, minority-owned food and retail vendors, and educational, community-focused, and family-friendly activities.
Website: ulhr.org/juneteenth
Norfolk Harborfest
When: June 19-23
Where: Downtown Norfolk waterfront
Festivities: Celebrating its 50th anniversary this year, this is a free, maritime event. Featuring the Parade of Sale, a 26-mile parade procession of more than 60 international tall ships and military vessels. Harborfest will also feature one of the largest fireworks displays on the East Coast, live music, national and regional engagement, Navy exhibits, and local artisan foods. A special “Parade of Cadets” is also scheduled for June 21.
Website: festevents.org/events/2026/norfolk-harborfest
Juneteenth Norfolk
When: June 19-21
Where: Town Point Park, Norfolk
Festivities: Juneteenth falls on June 19th each year, which perfectly lines up a weekend of celebrations. As a vibrant nod to unity and freedom, Juneteenth Norfolk will be part of those festivities, featuring live national and regional musical acts, fireworks, and food, in addition to educational, cultural, and heritage activities.
Website: festevents.org/events/2026/juneteenth-park
Jazzteenth
When:June 20
Where: 2405 Atlantic Ave., Virginia Beach Oceanfront
Festivities: Jazzteenth is a new signature experience that will bring world-class jazz and R&B, cultural arts, and community-centered programming to the heart of Virginia Beach, creating the first jazz festival of its kind on the Virginia Beach Oceanfront. The festival, headlined by R&B powerhouse Keke Wyatt and acclaimed soul singer Vivian Green, is designed to honor the historical significance of Juneteenth while celebrating the rich musical legacy that has long been part of the resort area and the broader Hampton Roads region. Planned elements for the event include national recording artists, cultural arts activations, educational and heritage-focused experiences, and community engagement opportunities.
Website: jazzteenthfestival.com
Newport News Juneteenth Freedom Festival
When: June 20
Where: Victory Landing Park, Newport News
Festivities: Held at the park on the James River at 26th Street, the Newport News Juneteenth Freedom Festival celebrates freedom and African American culture with live performances, educational exhibits, and family-friendly activities. Live music featuring national and local acts will be held throughout the day. The event is free to attend and open to the public.
Website: nnparksandrec.org/event/juneteenth-freedom-festival
Williamsburg Live
When: June 25–28
Where: Lawn of the Art Museums of Colonial Williamsburg
Festivities: The four-day event features national and regional musical artists. Guests will also enjoy a variety of food trucks, craft beer, and Virginia wine. This year’s lineup includes Melissa Ethridge & Wynonna Judd, along with Alison Krauss & Union Station. Tickets are available through the Virginia Arts Festival website.
Website: vafest.org/williamsburg-live
La Fiesta Virginia Beach
When: June 26-27
Where: 24th Street Park, Virginia Beach
Festivities: A two-day celebration of Latin culture held at the Virginia Beach Oceanfront, specifically featuring events at the 24th Street Park. With Latin music, dance performances, and food, events Friday are free to attend and open to the public. Tickets for Saturday’s performances are available on the La Fiesta website.
Website: beacheventsvb.com/event/la-fiesta-virginia-beach-2026
Barrett Baker
