Weekend in Portsmouth: One of America’s most charming Christmas towns

Last year, The WeekEnder kicked off the holiday season in a real-life snow-globe: New Hope, Pennsylvania. This year, we’re pointing our compass north to Portsmouth, New Hampshire, a seaport city that has been called one of America’s Christmas capitals. With all the twinkling lights, gingerbread houses, and holiday traditions, we couldn’t agree more.

“It’s like a Currier & Ives print come to life,” says Veronica Lester, director of marketing at Strawbery Banke Museum, a 10-acre living history museum that co-hosts an annual Vintage Christmas celebration and pulls out all the stops to help transform Portsmouth into a winter wonderland—from an outdoor skating rink to decorated historic houses to candlelight strolls.

But before we start unwrapping all the appeals of Portsmouth, let’s get a handle on the geography. This coastal town is divided into several sections: There’s Market Square (the commercial district smack in the center of it all), the West End (an up-and-coming area with restaurants and shops), and the South End (a magical residential neighborhood with narrow brick sidewalks and Colonial houses). Right outside town is New Castle, a quiet enclave spread across several islands that’s home to the top place to stay.

Portsmouth is rich in arts and culture, and one of the major players is The Music Hall, an historic performance space that co-hosts Vintage Christmas with Strawbery Banke Museum. Monte Bohanan, The Music Hall’s community engagement director, says the art scene is what drew him to Portsmouth. “I grew up an hour west of here and Portsmouth was always my cultural true north,” says Monte. “For such a small city, Portsmouth punches well above its weight when it comes to arts and culture and events.”

Thanks to trailblazers like David Vargas, a James Beard award-nominated chef, Portsmouth also has a buzzing food scene. David made a name for himself by fusing his Mexican heritage with the best New England ingredients at his restaurant, Vida Cantina. He also co-founded the New England BIPOC Fest, an annual fall festival that celebrates the Seacoast’s underserved cultures and communities with food, art, design, and more. David grew up in California and moved here with his wife, a New Hampshire native. What attracted him: “It’s absolutely beautiful and there are incredible chefs doing some amazing things for their community,” says David.

Now, let’s head to Portsmouth and start the holidays off right.

-Laura Begley Bloom, New York's Senior WeekEnder Writer

Set on a tiny island on the outskirts of town, this sprawling estate is a flashback to another era, with its red mansard roof, sprawling porch, elegant woodwork, and brass trimmings. The property was originally built in 1874 by a Boston-based distiller who wanted to create a grand vacation spot for New England vacationers—and his legacy lives on today. Wentworth goes all out for the holidays, starting on December 4 with Illumination, a special event where Santa and his elves light up the hotel and unveil a giant gingerbread house. Book a special holiday meal at Salt, the onsite farm-to-table restaurant.

For Instagrammers: Hotel Portsmouth - This converted 1881 Victorian mansion mixes a taste of the past (claw-foot tubs, fireplaces) with modern amenities. “Each room is unique and the folks who run it are great,” says Monte Bohanan.

For an affordable stay: Ale House Inn - Set in a 19th century brewery warehouse that closed during Prohibition, the Ale House is a cheery spot with sleek rooms.

For sweethearts: The Sailmaker’s House - A charming family-owned inn with a nautical vibe and an ideal location that's perfect for romantic strolls through Market Square and Prescott Park.

“What makes a difference in Portsmouth is that a lot of the chefs care about supporting their community,” says David Vargas. “And by supporting your local farms and your community, you’re not just eating good food, you’re eating good energy.”

Colby’s Breakfast and Lunch - “A tiny breakfast and lunch location that always has a line but is well worth the wait,” says Veronica Lester. “I’m a big fan of the blueberry pancakes with a side of bacon.”

La Maison Navarre - This pastry shop is run by a couple from France, who have brought a taste of Europe to Portsmouth—think addictive croissants, crêpes, and macarons.

The Friendly Toast - This kitschy scratch kitchen and bar serves brunch all day and is always packed, thanks to dishes like Churro Bites topped with strawberry habanero jam and the Snack, Crackle, Cluck sandwich with Rice Crispy-coated chicken breast.

Cup of Joe - A coffee shop by day that transforms into a bar with live music at night. “An incredible spot,” says David. “Not only is owner Joanna Kelley the president of the board for the BIPOC Fest, she’s also the first African American woman to be the assistant mayor for the city of Portsmouth."

Bennett's Sandwich Shop - A simple little hole-in-the-wall with awesome sandwiches like a shaved steak-and-cheese sub and a tuna melt to die for.

River House - Perfect for lunch with a view, this family-friendly surf-and-turf spot is set right on the water. “I love the cranberry walnut chicken wrap,” says Veronica.

The Wilder - A modern New England gastropub. “Always ask what the taco of the day is—they’re so delicious they often sell out,” says Veronica, who also recommends the nitro cold brew espresso martini.

Jumpin’ Jay’s Fish Café - If you’re in the mood for seafood, Jumpin’ Jay’s is a classic. “It’s my go-to for oysters, but I always get the pan-seared salmon,” says Monte Bohanan.

Raleigh Wine Bar + Eatery - “The owner, Nimi, knows her food and her wine,” says David. “The menu is ever-changing, but the last time I went, I had a veal pasta that was absolutely amazing.”

Vida Cantina - David’s award-winning modern-Mexican restaurant goes beyond the standards. Think mole jazzed up with squid ink and pozole made with corn, hominy, and winter squash. The restaurant is recognized for its tacos, thanks to the hand-pressed tortillas made by a local company that David originally founded. “It’s what helps stand us apart from any other Mexican restaurant around,” he says.

Street - This eclectic spot that has been featured on Diners, Dive-Ins, and Dives serves street food eats from around the globe, from falafel to phở, burgers to bibimbap.

Cava - “A tiny Spanish tapas restaurant with a handful of tables—you need to make a reservation,” says Monte.

Durbar Square - Traditional Himalayan food. “We in the chef community call it ‘the Hidden secret of Portsmouth,’” says David. “It’s my favorite date night for myself and my wife.”

Shalimar - “Incredible homemade Indian food,” says David.

Black Trumpet - Chef Evan Mallett (co-founder of the BIPOC Fest) is another Portsmouth visionary who serves memorable farm-to-table creations in a cozy brick building right on the water. “Their locally-sourced, rotating menu never disappoints,” says Veronica.

Ristorante Massimo - Fine Italian dining downstairs—perfect for a romantic date night. Upstairs is a more casual bar that Veronica recommends for a glass of wine and tasty small bites like the Formaggi, Salumi e Cicchetti.

There’s been a long history of artists in and around Portsmouth. “It’s the classic story—when things weren’t so economically great, that’s when the artists moved into the abandoned warehouses and began the renaissance that has continued until today,” says Monte Bohanan.

Strawbery Banke Museum - In 1623, English colonists established a settlement at Portsmouth Harbor and named it “Strawbery Banke”—legend has it—for the wild fruit growing along the banks of the river. The area has been converted into a living history museum that transforms into an immersive holiday experience with candlelight strolls and houses decked out for the season. Visitors can learn about what a Victorian Christmas was like in 1870 at the Goodwin Mansion or check out Hannukah in 1910 at the Shapiro House.

The Music Hall - At this intimate space with Broadway-quality productions, every seat in the house is a front-row seat. This season, there’s a special production of Elf, The Musical. Monte’s insider tip? “Check out the restrooms—the ladies room looks like it’s straight out of Harry Potter. It’s a fantastical Gaudí-esque space that transports you out of your day to day,” he says.

Portsmouth Historical Society - Founded in 1917, this nonprofit celebrates the area’s history, arts, and culture and also hosts an annual gingerbread house exhibition.

Seacoast African American Cultural Center - New Hampshire’s first Black cultural center showcases the contributions of individuals of African descent in the Seacoast community through concerts, art exhibits, and more.

3S Artspace - Part performance space, part contemporary gallery, part restaurant, this is a local art concept that’s on the vanguard.

The Players Ring - “A small theater that does mostly new works by regional playwrights,” says Monte. “Around the holidays, they showcase classics like A Christmas Carol.”

Jimmy’s Jazz and Blues Club - This restored landmark hosts national and regional jazz and blues acts, and has a serious culinary and cocktail program.

In addition to working and literally living at Strawbery Banke Museum—where she rents an apartment in one of the historic houses—Veronica Lester also works as a seasonal deckhand at Portsmouth Harbor Cruises (which operates summer sailing trips). What she loves about Portsmouth: “It’s a great walking city with tons of green spaces and a beautiful waterfront.” Here, some of the spots where the locals go when they want to get a breath of fresh air.

Labrie Family Skate at Puddle Dock Pond - A picturesque outdoor ice-skating rink with twinkling lights overhead and a firepit right on the ice.

Prescott Park - “As someone who is fascinated by all things maritime, this is a wonderful place to sit and watch the working tugboats and large ships sailing by,” says Veronica.

Urban Forestry Center - This forested loop is set right in the middle of Portsmouth. “If you’re looking for a woodsy hike, this is the place,” says Monte.

Besides all the charming shops, there’s another reason to go holiday shopping in Portsmouth: no state sales tax.

Portsmouth Soap Company - Homemade soaps, bath bombs, lotions, and indulgent gifts. “The two ladies who run this shop are incredibly nice and have a wealth of knowledge running occasional soap making classes, which are incredibly fun and doable for a beginner like myself,” says Veronica Lester.

Pickwick’s Mercantile - An old-fashioned shopping experience with apothecary items lining the shelves and staffers dressed in period costumes. “The place for trinkets, leather-bound journals, candles, Christmas items, Portsmouth-themed gifts, and more,” says Veronica.

Macro Polo - Fun gifts for anyone who loves a good laugh: toys, books, notecards, socks, you name it.

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