# Portsmouth Olde Towne Holiday Walk & Christmas Music Fest > Event for families in the Virginia Beach–Chesapeake–Norfolk area (VA / NC). Times are Eastern Time. - When: Sat, Dec 5 · 11:00 AM – 5:00 PM - Where: Olde Towne Portsmouth Historic District, High St & Court St, Portsmouth, VA 23704 - Ages: All ages welcome (Free historic street festival) - Price: Free admission; carriage rides and holiday treats available - Organizer: Olde Towne Portsmouth Merchants & City of Portsmouth - Official page: https://oldetowneportsmouth.com/events/ - Last checked: Thu, Nov 5 Source: Grassy Knees is a directory of real family events, places and programs for kids across major U.S. metro areas, where every listing is researched from the organizer’s own page and shows the date we last checked it. https://grassyknees.com covers 42 metro areas as of Nov 11, 2026, with more added regularly. About: https://grassyknees.com/about Freshness: listings are re-checked on a daily research run (latest check 2026-11-10), and new events are added as organizers post them. Sell-outs, weather cancellations and time changes show up on the live page first: https://grassyknees.com/virginia-beach/activities/portsmouth-olde-towne-holiday-walk-and-christmas-music-fest--listing-93883c8832c62bdb591399f7 ## About Step back in time to an authentic 19th-century Christmas during the Portsmouth Olde Towne Holiday Walk. The historic district's brick-paved sidewalks and gaslit streets are lined with historic homes and boutique shops lavishly decorated in real evergreen wreaths, velvet bows, and warm candlelight. Families can stroll along High Street while listening to strolling Victorian a cappella carolers dressed in authentic period attire, bagpipe ensembles, and brass quartets. Local merchants offer warm apple cider and gingerbread treats, while children can enjoy free horse-drawn carriage rides beneath twinkling tree lights, participate in a holiday scavenger hunt visiting historic landmarks, and greet Father Christmas at the historic Courthouse courtyard. Family Experience & Accessibility: • Stroller Accessibility: Brick sidewalks have smooth curb cuts throughout the historic High Street corridor; easy walking terrain for strollers and wagons. • Nursing & Rest Spots: Family restrooms and comfortable indoor resting spaces located inside the Portsmouth Cultural Arts Center and adjacent Children's Museum. • Age Suitability: Wonderful multi-generational outing for babies, toddlers, school-age kids, and history-loving grandparents. • Sensory Tips: Nostalgic, gentle acoustic music without loud amplification; charming gaslamp ambiance provides a calm, warm evening experience. ## Similar picks in Virginia Beach - [Holiday Yule Log Bonfire & Christmas Marketplace at Town Point Park](https://grassyknees.com/virginia-beach/activities/holiday-yule-log-bonfire-and-christmas-marketplace-at-town-point-park--listing-1c12b408b1b7f37985ab545c) — Sat, Dec 5 · 12:00 PM – 8:00 PM · Town Point Park, Norfolk · All ages · Free · checked Nov 7. 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