Illustration of a generic other scene (Olde Towne Holiday Music Festival)
Other Christmas Activities

Olde Towne Holiday Music Festival

Visitors can stroll along High Street to enjoy festive entertainment staged throughout the area. Performances take place both indoors and outdoors across local businesses, restaurants, and churches.

What to Expect

Live holiday entertainment hosted along High Street in Olde Towne.

Event Details

Ages

All ages

Neighborhood

Olde Towne

Timed Entry

No

Organizer

City of Portsmouth Parks and Recreation

Local Insight & Ratings

Family Friendly

🎄 🎄 🎄 ⚪ ⚪ (3/5)

Best For

Live-music fans and olde towne strollers

Vibe

Festive and musical

Energy Level

Moderate

Photo Friendly

Moderate

Weather Sensitivity

Moderate

Location

High Street
Portsmouth, VA

Know Before You Go

  • Hours: 11am- 3pm; additional entertainment until 5:00pm.

Tips & Advice

  • Duck into the businesses, restaurants and churches along High Street, because many of the performances happen indoors as well as out on the street.
  • Stay on after the main festival ends, since extra entertainment keeps going at businesses, restaurants, churches and other spots nearby.
  • Add a stop at the Winter Wonderland: Coleman Collection at the Portsmouth Art and Culture Center, which has its own admission for all ages.
  • Dress warmly for a December day, since part of the entertainment is staged outdoors along High Street.

Special Events & Promotions

  • Winter Wonderland: Coleman Collection at the Portsmouth Art and Culture Center, with its own admission for all ages.

Quick Actions

Frequently Asked Questions

What kind of entertainment is there?

Holiday performances are staged along High Street, both inside and outside businesses, restaurants and churches.

Who puts on the extra performances?

The Olde Towne Business Association, PortsEvents, and Museums and Tourism add more entertainment along High Street and at other spots nearby.

Does anything keep going after the main festival?

Yes. The extra entertainment at businesses, restaurants, churches and other spots carries on after the main festival on High Street ends.

Is there anything else to see while I'm there?

Stop by the Winter Wonderland: Coleman Collection at the Portsmouth Art and Culture Center. It has its own admission and is open to all ages.

Tags

live musiccommunity celebrationfamily friendlyseasonal activitiesholiday traditionfestive atmosphere

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Always check the official website for the most current information.

We've done our best to keep details up-to-date, but event schedules, prices, and policies can change. For the latest updates, please visit the official website or contact the organizers directly. Christmas Events Near Me is an independent guide and isn't affiliated with the events we list.

Contributors & Updates

Last Updated: Oct 20, 2026
Original Submitter: Sep 17, 2025 The Christmas Events Near Me editorial team