Tag: Live Music

Olde Towne Holiday Music Festival

The Olde Towne Holiday Music Festival began in 1998 and has become the signature holiday event for the City of Portsmouth. In 2022, this special day of music and friendship takes place on Saturday December 10th, from 11 AM until 5 PM. You’ll find even more music in restaurants, bars, and churches after the festival officially ends. The Farmer’s Market opens at 10 AM. So, spend the day and enjoy the sounds of the holiday season and support the local shops and restaurants.


11:00 AM
Soul Intent – High and Court Streets
Churchland High School Performing Arts Dancers – High and Washington Streets
Brighton Elementary School Chorus – Portsmouth Welcome Center
Parkview Elementary School – Middle Street Mall

11:30 AM
Douglas Park Elementary School – High and Washington Streets
Churchland Elementary School Chorus – Portsmouth Welcome Center
Churchland Academy Chorus – Middle Street Mall

12:00 PM
Tidewater Concert Band – High and Court Streets
Amy Kaus (until 2 PM) – Market Street General Store
All City Performing Arts Ensemble (Middle School) – High and Washington Streets
Waterview Elementary Chorus – Portsmouth Welcome Center
Victory Elementary School Chorus – Middle Street Mall

12:30 PM
2nd Wynd – High and Court Streets (until 1:30 PM)
Celtic Fiddle Music at Winter Wonderland – Portsmouth Art and Cultural Center (until 4 PM) – $3 admission
Simonsdale Elementary School – High and Washington Streets
Churchland Primary & Intermediate Chorus – Portsmouth Welcome Center
Hodges Manor Elementary School Chorus – Middle Street Mall

1:00 PM
Southside Community Concert Band – Monumental United Methodist Church
Lakeview Elementary School Chorus – High and Washington Streets
Cradock Elementary School Chorus – Portsmouth Welcome Center
Westhaven Elementary School Chorus – Middle Street Mall

1:30 PM
Tidewater Concert Band – High and Court Streets
I.C. Norcom High School Choir – High and Washington Streets

2:00 PM
Brasswind – High and Court Streets
Effigies – Roger Browns
Manor High School Chorus – High and Washington Streets

2:30 PM
Churchland High School Chorus – High and Washington Streets

3:00 PM
Chris Cushna Piano – The Book Club

3:30 PM
Holiday Wind Ensemble – Anderson Wright
AA Batteries – Stellar Wine
Tidewater Winds Holiday Concert _ Monumental United Methodist Church

4:00 PM
Mike Caggiano Piano – The Book Club

Doorway Singers – 11 AM – 3PM
Colonial Carolers – 11 AM – 5 PM
Holiday Brass Quintet – 3:30 PM – 5 PM
James Wood – Violin 2 PM – 5 PM


Holiday Sing Along – Portsmouth Art & Cultural Center 5:30 PM – Free
Caroling Through Olde Towne with Father Christmas – Middle St Mall 6:00 PM – Tickets $25 – Purchase Now


Roaming Christmas characters for kids – 12 PM – 2 PM
Children’s Bounce House – 11 AM – 3 PM
Marshmallow roasting on the street corners – Portsmouth Fire Department – 11 AM – 3 PM
Holiday Homes Tour – Historic Olde Towne Neighborhood – 1 PM – 6 PM – Tickets $15 – Purchase Now
Winter Wonderland: The Coleman Collection – Portsmouth Art & Cultural Center – 12 PM – 8 PM – $3
The Coleman Collection Nativity Scene – Monumental United Methodist Church – 11 AM – 5 PM – Free
Children’s Christmas Shoppe – Trinity Church- Reservations Required 9 AM – 4 PM
Make and Take – Painted Glass Ornaments – Portsmouth Art & Cultural Center Annex – Free with admission to Winter Wonderland
Snow Wonders – Middle Street Mall – 6 PM – Free

Virginia Handbell Consort Holiday Concert

It’s the 84th Season of the Portsmouth Community Concerts. Tickets are $25 each. Concerts are held inside the beautifully restored auditorium at Churchland High School.
Formed in the fall of 1996, the Virginia Handbell Consort became the first community handbell ensemble in the Hampton Roads area. Their auditioned musicians perform on handbells, hand chimes, and a variety of other percussion instruments. Under the direction of Al Reese, the Virginia Handbell Consort displays a stunning demonstration in the art of English handbell ringing, an art that is beautiful to hear as well as fascinating to watch. Their concert repertoire is a mix of sacred, classic, contemporary, show tunes, and big band swing
designed to showcase their unique instrument. Part of their mission is to demonstrate to audiences that while handbells are a part of the holiday season’s traditions, they are not limited to holiday performances. They are a year-round source of entertainment. Some notable performances include Kennedy Center’s Millennium Stage, Handbell Musicians of America’s 50th Anniversary Showcase Concert, Ferguson Center’s Home for the Holidays, Fort Monroe Holiday Concert with the U.S. Army TRADOC (Training and Doctrine Command), Williamsburg’s First Night, and with the Virginia Symphony Orchestra

Olde Towne Holiday Market & Tree Lighting

Enjoy a hometown holiday tree lighting complete with decorations, music, the Snow Queen, Father Christmas, and even a little snow! Additionally, the Olde Towne shops will be open late and 20 crafters & authors will be selling their wares. There will also be a free Tidewater Winds Quartet concert, strolling colonial carolers, hot cider, prize drawings, and shuttle rides. You can be sure to get in the holiday spirit right here in Olde Towne!

High Street Corridor 4 – 8 pm
Olde Towne Merchants’ Holiday Open House

Monumental United Methodist Church 4 – 7 pm
Coleman Collection Nativity Scene and hot apple cider

Anderson-Wright Rooms & Gardens 5 – 8 pm
Tango Music & Dancers Hot Apple Cider and Ginger Snaps

Oxford Square Washington & High Street 6:15 – 7:30 pm
Holiday Quintet

Trinity Episcopal Church 7:30 pm
Tidewater Winds Woodwind Quartet Free Concert

Middle Street Mall 4 – 7 pm
Crafters Market with 20 crafters and local authors

Children’s Museum Holiday Member Night 5 – 7 pm
Museum Exhibits available. Enjoy a special holiday-themed Make It, Take It art activity, and a showing of A Charlie Brown Thanksgiving. Reserve your tickets! Members should reserve tickets under Portsmouth Museum Member. You can reserve up to the maximum tickets allowed for your membership level.

Southside Community Band 5 – 5:45 pm
Please bring a new unwrapped toy for Toys for Tots

Holiday Tree Lighting Program 6:30 – 7 pm
The Snow Queen, Father Christmas, the Grinch, the Colonial Carolers, and even a little snow!

Strolling Entertainment 4 – 8 pm
Father Christmas, Rabbi Atschul, and Babu will be sharing songs and stories of Christmas, Hanukkah, and Kwanzaa. The Snow Queen and Snow Sprite will delight children with tales of the South Pole and their encounter with the Sugar Plum Fairy. The Colonial Carolers and the Colonial Kids will fill the business district with songs of the season and holiday cheer!
A strolling violin player will share holiday favorites.
Free rides on the Olde Towne Shuttle so you don’t miss any of the fun!

These Olde Towne shops are open late and decked out for the holidays:

  • Scoops!
  • Olde Towne Arts & Music
  • That Art Store
  • MM Rockin
  • Children’s Museum Gift Shop
  • Portsmouth Welcome Center
  • The Coffee Shoppe
  • Little Shoppes on High
  • Market Street & General Store
  • Sole Right Men’s Fine Footwear
  • Village Thrift
  • Blahzay Boutique
  • Bier Garden Gift Shop
  • Way Back Yonder Antiques
  • Studio CK Salon
  • The Book Club
  • Anderson-Wright Rooms & Gardens
  • Love More
  • Kitchen Koop

Make sure to get a free raffle ticket from each location to be entered in a drawing for one of our great prizes!

Olde Towne Market Day

Olde Towne Market Day is actually 7 markets rolled into one!  Spend the day on High Street and enjoy the shops and restaurants as well as all of these wonderful outdoor markets:


Portsmouth Olde Towne Farmers Market

9 a.m. – 2 p.m. High and Court



Get Colorful and Paint Your Hearts Out

9 a.m. – 2 p.m. High and Green



Gently Viewed Art Sale

The Ida Kay Jordan Collection

9 a.m. – 2 p.m. High and Green



Komi Art Market

9 a.m. – 2 p.m. High and Court



First Saturday Presents

Creative Thunder Bantaba

10 a.m. – 12 p.m. Portsmouth Art & Cultural Center



Olde Towne Antique & Flea Market

10 a.m. – 2 p.m. Middle Street Garage



Olde Towne Spring Market

11 a.m. – 3 p.m. Middle Street Mall



Portsmouth Palooza (all day musical entertainment)

11 a.m. – 4 p.m. Middle Street Mall


Free Admission to the gallery at the Portsmouth Art & Cultural Center and to the Portsmouth Naval Shipyard Museum.  10 a.m. – 4 p.m.