Vintage Christmas Events in Portsmouth

Get your holiday fix at the many festive Vintage Christmas events happening throughout December in Portsmouth.

Photo by David J. Murray/Clear Eye Photo

One town in New Hampshire really pulls out all the stops for Christmas with a month of events that range from musical performances to ice skating.

Vintage Christmas once again showcases the magical Candlelight Stroll, now in its 40th year, at Strawbery Banke Museum and live holiday shows at The Music Hall’s landmark Historic Theater and the intimate Music Hall Loft on Congress Street. It all takes place in elegant and festive downtown Portsmouth, which also happens to have some excellent independent stores for Christmas shopping.

Get ready to cuddle up with a free trolley ride through Market Square, stroll through the snowflakes to the many eclectic shops, step back in time to welcome “The Winter Visitor” through 300 years of living history at the festively decorated Strawbery Banke Museum Candlelight Stroll, or enjoy a first-class show at The Music Hall. Back by popular demand — the free Vintage Christmas Trolley shuttles patrons around the historic seaport each Saturday and Sunday afternoon and evening for the first three weekends in December.

Here are a few of this year’s events:

November 27-December 22: “Annie

“Annie” is the heartwarming and hilarious story of a merry, quirky orphan girl finding a home for Christmas, featuring Broadway actors and dancers. Sally Struthers’ show-stealing Miss Hannigan is back in a production that will knock your socks off. With a memorable cast of characters, and beloved songs “Tomorrow” and “It’s a Hard Knock Life,” this is truly a family-friendly musical. Bring Annie home for the holidays.

2019 “Annie” show times:

  • Wednesday, November 27, 2 p.m.
  • Wednesday, November 27, 7:30 p.m.
  • Friday, November 29, 2 p.m.
  • Friday, November 29, 7:30 p.m.
  • Saturday, November 30, 2 p.m.
  • Saturday, November 30, 7:30 p.m.
  • Sunday, December 1, 12 p.m.
  • Sunday, December 1, 4:30 p.m.
  • Wednesday, December 4, 2 p.m.
  • Wednesday, December 4, 7:30 p.m.
  • Thursday, December 5, 7:30 p.m.
  • Friday, December 6, 7:30 p.m.
  • Saturday, December 7, 2 p.m.
  • Saturday, December 7, 7:30 p.m.
  • Sunday, December 8, 12 p.m.
  • Sunday, December 8, 4:30 p.m.
  • Wednesday, December 11, 2 p.m.
  • Wednesday, December 11, 7:30 p.m.
  • Thursday, December 12, 7:30 p.m.
  • Friday, December 13, 7:30 p.m.
  • Saturday, December 14, 2 p.m.
  • Saturday, December 14, 7:30 p.m.
  • Sunday, December 15, 12 p.m.
  • Sunday, December 15, 4:30 p.m.
  • Wednesday, December 18, 2 p.m.
  • Wednesday, December 18, 7:30 p.m.
  • Thursday, December 19, 7:30 p.m.
  • Friday, December 20, 7:30 p.m.
  • Saturday, December 21, 2 p.m.
  • Saturday, December 21, 7:30 p.m.
  • Sunday, December 22, 10 a.m.
  • Sunday, December 22, 2 p.m.

The Music Hall is located at 28 Chestnut St. in Portsmouth. Visit The Music Hall for tickets and more information.

Every day in December: Labrie Family Skate

The entire family will love skating at Strawbery Banke’s Puddle Dock Pond, a seasonal outdoor ice skating rink at the heart of the 10-acre living history museum. Puddle Dock Pond at Strawbery Banke opens in late November/early December (weather permitting) and will be in full operation, seven days a week, Sun to Tues 10 a.m. to 7 p.m., Wed 11 a.m. to 7 p.m., Thurs 10 a.m. to 7 p.m., Fri 7 a.m. to 9 p.m. and Sat 9 a.m. to 9 p.m. throughout December and on through New Year’s Day and the months of January and February.

Puddle Dock Pond offers 12,500 square feet of professionally maintained ice surface combining an 80-by-125-foot oval and a 60-foot diameter circle, all surrounded by a post and rail fence. A seasonal pavilion houses ticketing and skate rentals. The Figtree Kitchen Cafe in the adjacent museum Tyco Visitor Center serves food and beverages. Puddle Dock Pond offers public skating (including several free sessions each week), pond hockey for children and adults and skating lessons for all ages. Skate rentals and sharpening services are available. For details, schedules and more information, visit

December 7: Portsmouth’s Illuminated Holiday Parade

Tree lighting – 5:30 p.m.
Parade – 6 p.m.
Rain date is December 8.

Count down to the tree lighting in Market Square and stay for the illuminated holiday parade that winds through the heart of Portsmouth.

The Portsmouth Illuminated Holiday Parade and Tree Lighting Ceremony. Photo by David J. Murray/Clear Eye Photo

December 7-8, 14-15 and 21-22: The Candlelight Stroll

Stroll through life in a simpler time as 350 years of American history, winter traditions and holiday celebrations unfolds around you in New Hampshire’s oldest waterfront neighborhood. Costumed role-players greet you in the historic homes where you are invited to rediscover the joys of simpler times. Mrs. Shapiro prepares a Hanukah celebration her 1919 Russian Jewish kitchen. Mrs. Goodwin, her family and servants prepare a Victorian Christmas. Father Christmas, the night watchman, “Mayor Frank Jones” and other role-players make their rounds along the dirt lanes, and the Abbotts await news of their soldier fighting in Europe in the Second World War. You’ll also enjoy the carolers, Christmas crafts and more sights, sounds and smells of the holidays.

Step back in time at the delightful Strawbery Banke Museum Candlelight Stroll.

Ticket prices for the Strawbery Banke Candlelight Stroll are $20 for adults, $7.50 for children and $55 for families (two adults and their children ages 17 and under). Tickets can be purchased online at or by phone at (603) 433-1107. From 5 p.m.-9 p.m. on Saturdays and 4 p.m.-8 p.m. on Sundays. Puddle Dock Pond skating and Candlelight Stroll bundles are also available.

December 27-29: Juston McKinney’s Last Laugh 2019

End the year with laughter as the Seacoast’s own Juston McKinney performs three hilarious nights at The Music Hall. He has appeared on “The Tonight Show with Jay Leno,” “Conan O’Brien” and has two Comedy Central specials including his own one-hour special. He has also been named Best Comedian of NH by New Hampshire Magazine. Have the last laugh of 2019 with Juston as he dishes on New England life and looks back at the year that was. Tickets are $26. The Music Hall, 28 Chestnut St. See the website for tickets and more information.

Learn More

Want even more Vintage Christmas information and events? Click here for a complete schedule and more information.

Categories: Holiday Guide Events