8 U.S. Towns for Boutique Holiday Shopping Getaways

Discover festive American streets and neighborhoods for unique gifts and seasonal cheer

people walking with a holiday market sign and skyscrapers in the background

Unique streets and neighborhoods around the country make great holiday getaways, where travelers can enjoy seasonal events and complete their holiday shopping. Among them: Boston’s Seaport neighborhood, which hosts the Snowport Holiday Market.

Boston Seaport by WS

Berit Thorkelson,

AARP

Published November 07, 2025

Good news: There’s a way to shrink December’s to-do list and have holiday fun in the process.

Introducing the shopping getaway. To build one, you’ll need a concentrated cluster of independent shops anchoring a neighborhood that celebrates the season with loads of sparkle and cheer.

The final key ingredient is your favorite shopping companions. After all, it’s important to stay connected with those we love over the holidays, especially as we age. The U.S. surgeon general’s 2023 advisory, “Our Epidemic of Loneliness and Isolation,” states that social connection is as vital to survival as food and water, enhancing cognitive function, improving mental well-being and protecting against mental and physical illness, including cardiovascular disease, dementia and stroke. In short, social connection can lead to a healthier, longer life — effectively increasing the amount of holidays in your future.

If that sounds like a valid excuse to go shopping with your friends, check out these eight destinations around the country. All are proven holiday hosts, ready to set you up with spot-on presents and lots of memory-making revelry — the proverbial bow on top.

people looking at a storefront with holiday decorations

More than 125 independently owned shops, along with their beautifully decorated storefronts, draw shoppers to walkable downtown Galena, Illinois.

Courtesy Galena Country Tourism

Main Street in Galena, Illinois

Amy Kraynak, a Chicagoan who writes about travel and life on her website Later Ever After, was a teenager when she first visited Galena during the holidays, with her parents and grandparents. All generations fell so in love with the slow-paced town, with its cobblestone streets and low-slung 19th-century brick buildings, that the seasonal trip has now become a nearly 30-year multigenerational tradition.

Visits here focus on the walkable downtown and its more than 125 independently owned businesses, including several home-store standouts. “My entire house has Christmas decorations from Galena,” says Kraynak. The town maintains a calendar of holiday events, including the Snowflakes and Sweets Stroll, an Ugly Sweater Food Tour, and the Night of the Luminaria and Living Windows, which Kraynak recommends. “Everything is lit in candles,” she says. “The town is literally glowing, and it’s just so magical.”

Holiday shopping in the Danish enclave of Solvang, California, is deliciously supplemented with home-baked pastries including aebleskiver, topped with powdered sugar and jam.

SolvangUSA

Copenhagen Drive in Solvang, California

Solvang’s Danish roots are evident in its half-timbered buildings, wooden windmills and traditions, including Julefest, a celebration running from Nov. 28 through Jan. 4. Among the activities happening on and around the main artery of Copenhagen Drive: a nightly light-and-music show, candlelight city tours and an evening Maker’s Market on the first three Wednesdays. Cindy Anderson, a boomer, has often visited from her nearby Santa Barbara home over the years. “A trip to Solvang at the beginning of December kind of gets you in the Christmas spirit,” she says.

Anderson enjoys wandering from shop to shop along Copenhagen Drive, prioritizing a stop at The Solvang Restaurant’s walk-up window for aebleskiver, ball-shaped pastries topped with powdered sugar and jam — a Danish Christmas treat served all year long in Solvang. Another popular holiday stop that sits just off Copenhagen: The Jule Hus, which has specialized in Old European ornaments since the 1960s.

The annual Holiday Promenade in the East Village neighborhood of Des Moines, Iowa, features carolers, free trolley rides and lots of local shops, including Storyhouse Bookpub, shown here.

Courtesy Greater Des Moines Partnership

East Village neighborhood in Des Moines, Iowa

The Des Moines River separates downtown proper from the East Village, a patchwork of renovated 100-year-old buildings filling roughly 12 blocks between the river and the gold-domed Capitol. The neighborhood went from run-down to vibrant over the past couple of decades, and now it’s buzzing with places to live, eat, drink and shop — think high-end boutiques, stationery shops, art galleries and more.

On Friday evenings from Nov. 21 through Dec. 19, the district hosts the Holiday Promenade, when shops offer specials and stay open late, carolers wander the streets and trolley rides are free. Gen Xer Kathy Barnes, who lives in Des Moines, describes the event as “a happy break in the Christmas season,” full of lights, music, snacks and great people-watching. “It’s the best shopping and a great mood-lifter during a month of what can feel like endless holiday obligations,” she says.

a historic courthouse lit up in festive colors

Court Square and its stunning 1892 brick courthouse anchor the holiday shopping and festivities in Bardstown, Kentucky.

Grizzly Media

North Third Street in Bardstown, Kentucky

Bardstown transforms into the North Pole of Kentucky during the holidays, with Court Square’s 1892 brick courthouse-turned-visitors’ center at the heart of the celebration. The square and the surrounding historic district are decorated with greenery and lights, including North Third Street, a small, walkable strip of independent boutiques and specialty shops branching off from the square. Here, visitors find locally made goods, build-your-own candles and bourbon-themed gifts. Bardstown is known as the Bourbon Capital of the World, after all.

Holiday events are plentiful and ongoing, including guided tours of My Old Kentucky Home, a 200-year-old mansion dressed up for the holidays, and cocoa and carols aboard My Old Kentucky Dinner Train.

holiday shoppers walking past a storefront

Holiday lights and luminaries create a festive backdrop for shoppers along popular Washington Avenue in Cedarburg, Wisconsin.

Courtesy Cedarburg Chamber of Commerce

Washington Avenue in Cedarburg, Wisconsin

Limestone and cream-colored brick buildings, plus a couple of historic mills once powered by the town’s Cedar Creek, give Cedarburg a storybook charm that’s even more striking when it’s twinkle-lit for the holidays. More than 70 boutiques, specialty stores, galleries and breweries line Washington, offering unique gifts, handmade art, home décor and seasonal treats.

On Fridays from Nov. 21 through Dec. 19, shops stay open late, and free trolleys shuttle shoppers up and down the avenue, decorated with thousands of luminaries, while live music fills town pubs and restaurants. Among the many other holiday events: the Cedarburg Artists Guild’s annual Holiday Art Fair, featuring handmade jewelry, fiber arts, ceramics and more, is held Dec. 5 to 7.

Visitors come for the lights, live music, food trucks and shopping booths, featuring the work of more than 125 makers, at the Snowport Holiday Market in Boston’s Seaport neighborhood.

Boston Seaport by WS

The Seaport in Boston

Boston’s Seaport District has transformed from an industrial waterfront into a trendy hot spot that embraces the harbor. From Nov. 7 through Dec. 28, it hosts the Snowport, including an outdoor holiday market featuring more than 125 vendors, along with live music, custom cocktails, and events such as curling and a menorah lighting. During a visit, Aline Boucher Kaplan, 78, enjoyed browsing the handmade scarves and Christmas ornaments and simply soaking in the holiday atmosphere. “There’s a sense of excitement and energy there that’s really fun to be part of before the holidays,” she says.

people sitting in a festive horsedrawn carriage

Natchitoches, Louisiana, becomes the “City of Lights” during the holidays, when charming Front Street bustles with shoppers and holiday festivities.

Courtesy Natchitoches Convention & Visitors Bureau

Front Street in Natchitoches, Louisiana

Natchitoches (pronounced NACK-a-tish) is hosting its 99th holiday festival, when it becomes the City of Lights, thanks to 300,000 twinkling lights and more than 100 illuminated set pieces. These lights and displays decorate downtown’s charming brick-lined streets, wrought-iron balconies and Cane River Lake shoreline.

The action is centered around the riverbank and Front Street, with indie boutiques, specialty stores and antique shops, as well as Saturday fireworks shows, parades and live entertainment throughout the season, from the Saturday before Thanksgiving until Jan. 6. Shopping opportunities expand with the Fleur de Lis Christmas Craft Market on Nov. 29 and the Mistletoe Market on Dec. 6.

santa, mrs claus and rudolph the red nose reindeer on a balcony

Santa illuminates downtown Ashland, Oregon, to kick off the Festival of Light, centered on the local shops and holiday events along Main Street.

Bob Palermini

Main Street in Ashland, Oregon

During the Grand Illumination, Santa and company arrive at this modern mountain town in a parade the day after Thanksgiving. Then, from a balcony overlooking a crowd of thousands, he leads a countdown to turn on a million twinkling holiday lights. The event kicks off the Festival of Light and creates a magical backdrop for a flurry of holiday activities — shopping included.

On the weekend, groups of carolers serenade shoppers on Main Street, which is home to dozens of locally owned gems. Standouts include a fiber arts store, a culinary shop with specialty gadgets and ingredients, multiple bookstores and The Drift Collective, a shop full of southern Oregon makers’ handmade pottery, jewelry, upcycled clothing and more. New to the festival this year: the Holiday Sip & Shop event on Dec. 6, with cozy drinks and in-store experiences.

%{postComment}%

Berit Thorkelson is a travel writer and editor for aarp.org. She has also written for publications such as National Geographic Traveler, Better Homes & Gardens and The Minnesota Star Tribune’s travel section.