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Olde Towne Holiday Music Festival 2021

November 22, 2021
Colonial Carolers perform on High Street

The Sound of the Holiday Season

The Olde Towne Holiday Music Festival began in 1998 and has become the signature holiday event for the City of Portsmouth. In 2021, this special day of music and friendship takes place on Saturday December 11th, 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.

Schedule of Events

Collage of musicians performing at the Olde Towne Holiday Music Festival 202111:00

  • Court Street Stage:  Original Rhondels
  • Strolling:  Doorway Singers
  • Strolling: Colonial Carolers
  • Inside Winter Wonderland: Colin McGlynn Celtic Fiddle
  • Kids Area (Middle Street):  Bounce House and Games
  • Cambridge Hall Open House (441 Washington St)
  • Marshmallow Roasting and Fire Pits
  • Farmers’ Market
  • Komi Art Market; 601 Dinwiddie
  • Baron’s Pub: Visit with Santa
  • Peace and Grind: Pop Up Shop and Book Signing (9 yo author)
  • Photos with Santa at Goodin Brothers Visual Arts Studio (516 Middle St)
  • Nativity display from the Coleman Collection: Monumental Methodist Church
  • Children’s Christmas Shoppe at Trinity – Schedule Your Appointment to Shop
  • Portsmouth Art & Cultural Center:  Winter Wonderland : The Coleman Collection – Get Tickets Here

 

 

 

 

Olde Towne Holiday Music Festival Performers Collage12:00

  • Court Street Stage:  Michael Clark Band
  • Washington Street: Tidewater Concert Band
  • Monumental Methodist: Southside Concert Band
  • Strolling: Doorway Singers
  • Strolling: Characters (Grinch, Snowman, Reindeer)
  • Cambridge Hall Open House (441 Washington St.)
  • Kids Area Middle Street: Bounce House and Games
  • Marshmallow Roasting and Fire Pits
  • Farmers’ Market
  • Komi Art Market: 601 Dinwiddie
  • Photos with Santa at Goodin Brothers Visual Arts Studio (516 Middle St)
  • Nativity display from the Coleman Collection: Monumental Methodist Church
  • Peace and Grind: Pop Up Shop and Book Signing (9 yo author)
  • Children’s Christmas Shoppe at Trinity (appt only)
  • Portsmouth Art Center:  Winter Wonderland : The Coleman Collection

 

 

 

Grinch character in a Santa costume1:00

  • Court Street Stage: Better By Tuesday
  • Washington Street: Tidewater Concert Band
  • Portsmouth Jazz Experience at Cambridge Hall (441 Washington St)
  • Strolling: Doorway Singers
  • Strolling: Colonial Characters
  • Strolling: Costumed Characters (Grinch, Snowman, Reindeer)
  • Photos with Santa at Goodin Brothers Visual Arts Studio (516 Middle St)
  • Kids Area Middle Street: Bounce House and Games
  • Komi Art Market: 601 Dinwiddie
  • Marshmallow Roasting/Fire Pits
  • Peace and Grind: Pop Up Shop and Kids activities
  • Children’s Christmas Shoppe at Trinity (appt only)
  • Nativity display from the Coleman Collection: Monumental Methodist Church
  • Portsmouth Art & Cultural Center:  Winter Wonderland : The Coleman Collection

 

 

 

 

Christmas tree at High Street Landing with a ferry in background 2:00

  • Court Street Stage: Champagne Band
  • Roger Browns: Rocking the Holidays with the Original Rhondels
  • The Book Club: Chris Cushna
  • Portsmouth Jazz Experience at Cambridge Hall
  • Strolling: Doorway Singers
  • Strolling: Dixieland Band
  • Kids Area Middle Street: Bounce House and Games
  • Marshmallow Roasting and Fire Pits
  • Children’s Christmas Shoppe at Trinity
  • Portsmouth Art & Cultural Center:  Winter Wonderland : The Coleman Collection
  • Photos with Santa at Goodin Brothers Visual Arts Studio (516 Middle St)
  • Paint Your Own Christmas Tree (Twisted Art & More)
  • Nativity display from the Coleman Collection: Monumental Methodist Church
  • Komi Art Market: 601 Dinwiddie
  • Peace and Grind: Pop Up Shop and Kids activities

 

 

3:00

  • Roger Brown’s: Rocking the Holidays with the Original Rhondels
  • Griff’s: Holiday Brass Quintet
  • Stellar Wine:  Summer Jones
  • Anderson-Wright Rooms and Gardens: Clan MacCool
  • Portsmouth Jazz Experience at Cambridge Hall
  • Fannies Vintage:  James Wood
  • Hill House: High Holiday Tea (Sold Out)
  • Photos with Santa at Goodin Brothers Visual Arts Studio (516 Middle St)
  • Strolling: Dixieland Band
  • Strolling: Colonial Carolers
  • Children’s Christmas Shoppe at Trinity
  • Komi Art Market: 601 Dinwiddie
  • Peace and Grind: Pop Up Shop and Kids activities
  • Portsmouth Art & Cultural Center:  Winter Wonderland : The Coleman Collection
  • Nativity display from the Coleman Collection: Monumental Methodist Church

 

 

Christmas lights on tree; Children's Shop at Trinity Church; musicians playing in street

4:00

  • Roger Brown’s: Rocking the Holidays with the Original Rhondels
  • Bier Garden Patio:  AA Batteries
  • Olde Towne Public House:  Holiday Brass Quintet
  • Peace and Grind: Thaddeus Coffey
  • The Book Club:  Michael Caggiano
  • Portsmouth Arts Center Courtyard: Clan MacCool
  • Portsmouth Jazz Experience at Cambridge Hall
  • Komi Art Market: 601 Dinwiddie
  • Photos with Santa at Goodin Brothers Visual Arts Studio (516 Middle St)
  • Strolling: Dixieland Holiday Brass Band
  • Strolling: Colonial Carolers
  • Portsmouth Art Center:  Winter Wonderland : The Coleman Collection
  • Nativity display from the Coleman Collection: Monumental Methodist Church
  • Peace and Grind: Pop Up Shop and Kids activities

 

Olde Towne Holiday Music Festival logo5:00

  • The Festival officially ends however there will still be plenty going on to keep you engaged..
  • Peace and Grind: Thaddeus Coffey continues
  • St. John’s Church:  Flute and Harp Concert
  • Photos with Santa at Goodin Brothers Visual Arts Studio (516 Middle St)
  • Snow Wonders at 5:30 on the Middle Street Mall (every Friday and Saturday through Dec 18th)
  • Winter Wonderland

 

Map with legend for eventLater that Night

Stellar Wine: Sip and Soul Saturday 8 p.m. – 10 p.m.

Baron’s Pub: Diamond Hall, 8:30 pm – 11 pm

Portsmouth Art & Cultural Center: Winter Wonderland, 6 pm – 8 pm

Jeans & Jerseys Presented by Showtyme Entertainment at Roger Brown’s 10 p.m. – 2 a.m.

 

 

About the Children’s Christmas Shoppe

Children's Christmas Shoppe logo

 

 

Trinity Christmas Shoppe was started in 1994 in Portsmouth at Trinity Episcopal Church.
Our plan was to teach children to give as well as receive at Christmas time. We started out small and have grown to serving approximately 200 children each year.

The Shoppe is held on the second Saturday in December each year. It is open to children between the ages of three and twelve years old. Each child may select a maximum of ten gifts with the help of an elf (usually a teenager) who assists in selecting an appropriate gift for the names on their list. The gifts are then wrapped in order to be a surprise on Christmas morning.  The children pay $4 for each gift which is used to donate to children’s charities each year.  Out of an abundance of caution this year, the event is by reservation only.  Reserve your visit today.

 

About Winter Wonderland: The Coleman Collection

Winter Wonderland LogoFollowing a two-year absence, Winter Wonderland: The Coleman Nursery Collection returns to the Portsmouth Art & Cultural Center.  The galleries will soon be brimming with twinkling lights and animated yuletide displays that have drawn generations of visitors from across the region to join in the holiday traditions that began at the Coleman Nursery in Portsmouth.  The exhibit offers a visual treat of animated scenes, busy elves and enchanted forest with woodland animals.

Visit some of your favorites, Sleeping Santa, the candy factory, toy shop, and bakery.  On weekends, visit with Olde Towne Santa in the Victorian chalet, and enjoy seasonal activities of holiday crafts, activities, and music, that begins opening weekend November 26- 28th and continues on weekends through December 31st.  Tickets are $3 each.  Out of an abundance of caution, we require you to reserve your tickets and times in advance.  Everyone must have a ticket.  Under two is free but the space must be reserved with the rest of your party.  Most people spend between 45 minutes to an hour at the exhibit.

 

Make It A S’mores & Music Weekend Getaway

S'more made on open fireThe Renaissance Portsmouth-Norfolk Waterfront Hotel has a special offer for holiday getaways.  Get a special rate on a king or queen waterfront room that includes breakfast for two and a S’mores kit for roasting on the patio fire pits.  The view is the best city lights view in all of Hampton Roads!  Book your special weekend getaway directly with the Renaissance.  CLICK HERE TO CHECK AVAILABILITY AND TO BOOK YOUR ROOM.

You will find the Renaissance Portsmouth-Norfolk Waterfront Hotel where charming local history meets modern comfort. Ideally located in the heart of the historic arts and culture district, our hotel near Norfolk, VA wows guests with impressive Elizabeth River views, best enjoyed from each of our immaculately appointed guest rooms.

 

The 2021 Olde Towne Holiday Music Festival is sponsored by

Olde Towne Holiday Music Festival Sponsoring organization logos

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