12 Days Of Cheer In Portsmouth: Making This A December To Remember

The holiday season is officially here, and there’s no shortage of ways to soak up the magic in and around Portsmouth. To help get you in the spirit, we’ve rounded up a dozen festive ideas you can enjoy throughout the month — each one a fun, joyful way to celebrate the season close to home.

From twinkling light displays and holiday markets to cozy treats, local shopping spots, winter activities and seasonal shows, these 12 picks highlight what makes Portsmouth feel especially merry this time of year. Whether you check off one or all twelve, it’s all about slowing down, supporting local businesses and making memories.

1. Celebrate the season at the Candlelight Stroll at Strawbery Banke.

Candlelight Stroll is one of Portsmouth’s most beloved holiday traditions, and this year’s theme — Midwinter Melodies — brings classic winter songs to life across the historic Puddle Dock neighborhood. Families can explore more than 350 years of seasonal traditions as they wander candlelit paths, step inside furnished homes from 1795 through the 1950s and meet costumed roleplayers sharing stories of the families who once lived there. Outdoor carolers, fife-and-drum performances and roaming reenactors add to the atmosphere, while Ice Dance International presents Currier & Ives-inspired skating shows twice each evening (weather permitting). Note that parking is off-site, with only a limited number of accessible spots. Arrival times begin at 4:30 and 5:30 p.m. on select dates from December 5–21, with a special Daylight Stroll offered on December 14.

2. Ride the Vintage Christmas Trolley around downtown Portsmouth while you shop.

The free Vintage Christmas Trolley makes it easy for families to get around downtown during the holiday season, offering a continuous loop between major parking areas, local hotels, The Music Hall and Strawbery Banke Museum. The shuttle runs roughly every 15 minutes, so you can hop on and off while browsing shops, grabbing cocoa or exploring festive events without worrying about parking. Service pauses for the Illuminated Holiday Parade on December 6 from 4:00–9:00 p.m., then resumes afterward for the evening’s Shop & Stroll. Keep an eye on the full schedule of holiday events — from tree lightings to gallery walks and pop-up markets — to pair your ride with something fun happening in town.

3. Lace up for outdoor skating at Labrie Family Skate at Puddle Dock Pond.

Set beside the historic buildings of Strawbery Banke, Labrie Family Skate at Puddle Dock Pond offers a classic New England skating experience once the winter season begins. The rink typically opens sometime in December, inviting families to glide under the open sky while the surrounding centuries-old homes and museum buildings create a cozy backdrop. Tickets are released weekly on Sundays at 5:00 p.m. and can be purchased online or at the Lawrence J. Yerdon Visitor Center, where skate rentals are also available. The 2025–2026 opening date hasn’t been announced yet, so check the rink’s Facebook page for the latest updates.

4. Enjoy holiday performances at Jimmy’s Jazz & Blues Club.

Right in the heart of Market Square, Jimmy’s Jazz & Blues Club offers an intimate, state-of-the-art setting for live music. The venue blends classic jazz-club charm with modern acoustics and lighting, creating an atmosphere where you feel connected to the musicians on stage. December brings special holiday performances, including “Christmas Dreaming with Stella Cole,” “Jane Monheit: The Merriest Holiday Show” and “Sharon Jones: Holiday Stories and Songs” — plus the club’s popular Sunday Jazz Brunch if you prefer a daytime outing. Browse the events calendar to see what’s lined up during your visit and plan a night out that feels festive from start to finish.

5. Wander through the glowing Winter Wonders walk-through light show in nearby Eliot.

Just about 15 minutes from Portsmouth, Winter Wonders turns 14 wooded acres in Eliot, Maine, into a mile-long trail of immersive light displays featuring more than 2.5 million lights. Families can stroll at their own pace through interactive exhibits, new installations added for the season and gently rolling forest paths that feel especially magical under fresh snow. The experience takes roughly an hour and includes everything from illuminated tunnels to large-scale scenes designed to spark wonder in both kids and adults. Tickets are available online; check the current offerings before planning your visit.

6. Experience Irving Berlin’s ‘White Christmas’ at The Music Hall.

The Ogunquit Playhouse brings its beloved production of White Christmas back to The Music Hall this season, filling Portsmouth’s historic theater with big dance numbers, nostalgic songs and Broadway-level talent. Iconic hits like “Happy Holiday,” “Sisters” and “Blue Skies” anchor the show, while the staging and costumes give the whole performance that classic, old-Hollywood sparkle. Select dates run from December 3–21, making it an easy show to pair with a holiday dinner downtown or a stroll through Market Square. Browse the calendar early to find the performance that fits your family’s December plans.

7. Warm up with coffee and German pastries at Kaffee Vonsolln.

Kaffee Vonsolln is one of those snug, brick-lined cafés that feel extra inviting on a cold December day, especially when the smell of fresh coffee is drifting from the in-house roaster. The family-run shop serves small-batch, ethically sourced beans roasted on-site, along with homemade German pastries that make a perfect pairing for a winter morning treat. You can sip a classic cappuccino, try one of their cappuccino cocktails or bring your family in for something sweet while you take a break from holiday errands. If you’re shopping for a coffee lover this season, their freshly roasted beans also make thoughtful gifts — just ask the staff for tasting notes or recommendations.

8. Step into the whimsical world of Pickwick’s Mercantile.

Pickwick’s Mercantile feels a bit like wandering into a storybook, with cedar shelves, vintage-inspired displays and a Victorian flair that makes the whole space glow during the holidays. The shop is known for its eclectic mix of treasures — imported perfumes, old-fashioned candies, books, candles, soaps and beautifully packaged gifts — you won’t find in big-box stores. It’s the kind of place where you can linger with your family, discovering unexpected finds or chatting with staff who love helping shoppers find just the right present. Whether you’re hunting for stocking stuffers or a one-of-a-kind gift, a stop at Pickwick’s adds a little magic to any winter day downtown.

9. Grab a tasty winter pint at Earth Eagle Brewings.

Earth Eagle Brewings brings a laid-back, local vibe to Portsmouth, with a compact pub that’s perfect for warming up after a day out in the cold. As the city’s oldest operating brewery, it pours a fun mix of styles, from its crowd-favorite New England Gangsta IPA and Circling Birds DIPA to seasonal sours, porters, Belgians and herbal ales. The menu includes hearty, casual bites and house cocktails, so there’s something for everyone at the table, even if beer isn’t their go-to. With its friendly atmosphere and indoor–outdoor setup, it’s an inviting place to meet up with friends or recharge with your family between holiday outings.

10. Settle in with a new read at Portsmouth Book Nook.

Right in the heart of downtown, Portsmouth Book Nook offers a cozy, welcoming atmosphere that makes you want to browse a little longer. The shop has a well-curated mix of fiction, memoirs and children’s books, and the staff is known for giving spot-on recommendations whether you’re shopping for yourself or picking out a holiday gift. Families can browse together, explore the growing kids’ section or keep an eye out for upcoming story times, author events and book clubs as the store expands its programming. If you’re searching for something specific, they’re happy to special-order titles — just ask, and they’ll track it down for you.

11. Get creative with holiday projects at Firefly Pottery.

Firefly Pottery is a welcoming spot for hands-on fun, offering in-studio painting, clay work, wheel-throwing classes and glass fusing for all ages. The staff is wonderful with beginners, making it easy for you and your family to dive in, try new techniques and enjoy creating something seasonal. December brings extra charm with festive workshops, a 20th-anniversary celebration and an ugly-sweater ornament contest that runs throughout the month. Reservations are recommended, and their events page is the best place to find the holiday projects happening during your visit.

12. Discover artful gifts and seasonal finds at Nahcotta.

Holiday shopping feels a lot more inspiring at Nahcotta, where original artwork, prints and well-designed home goods are arranged in a way that makes every corner worth a second look. The space has evolved over the years, but its focus on meaningful, well-made pieces remains clear, from ceramics and textiles to small-batch gifts you won’t find anywhere else. It’s a lovely place to browse at a relaxed pace, especially if you’re hunting for something personal for the holidays or hoping to treat yourself to a little creative boost. Their holiday collection is updated throughout the season, so take a look online to see what’s new before stopping by.

Stay warm, shop local and enjoy every twinkling moment — happy holidays, Portsmouth!

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