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Shop Till You Drop at America’s Best Cities for Holiday Shopping

Photo by Romrodphoto via Shutterstock
Written by Chris Osburn

This blog post was updated on December 23, 2019.

Silver bells! It’s Christmastime in the city! That means shopping for big bargains and perfect presents and having festive fun along the way. So if you’re wondering which US cities are the absolute best for taking a holiday retail wander then check out this all nice/not naughty list of the choicest shopping destinations in America.

Baltimore, Maryland

Inner Harbor Baltimore

Compact and quirky Baltimore is an ideal setting for urban retreats and shopping sprees anytime of the year – and that goes double in November and December. From awesome indie comic shop Atomic Books to Ma Petite Shoe (a gourmet chocolate and designer shoe boutique), you’ll find great success picking up gifts for even your most finicky friends and family. By the way, hometown heavyweight Under Armour has its Brand House in town and its Factory House just a short drive away in Curtis Bay.

Columbus, Ohio


Who knew Columbus was fast becoming a haven for fashionistas? Plenty of clued-in Columbusites and recent visitors to this friendly Midwestern town, that’s who! Believe it or not, Columbus has one of the nation’s highest concentrations of fashion designers. In fact, the city comes in third, right behind New York and Los Angeles. Big brands such as DSW and Abercrombie & Fitch call the city home, as do a growing number of chic boutiques and indie retailers. The area has more than its fair share of shopping centers and malls, including Tanger Outlets with more than 90 shops. ‘Tis the season? ‘Tis the town!

Jacksonville, Florida

Jacksonsville Florida Skyline

A mild winter on the beach in a one of Florida’s favorite towns plus some of the best shopping on the East Coast make Jacksonville a smart place to keep in mind for holiday shopping. Whether you go local buying prezzies at the boutiques in the trendy (and pedestrian-friendly) neighborhoods of San Marco, Avondale, Riverside, and Five Points or make a bee-line for the renowned bargains at the outdoor outlet mall St. Johns Town Center and the other popular malls in and around town, you’ll be spoiled for choice.

Minneapolis, Minnesota


Shopaholics would do wise to travel to Minneapolis, a retail wonderland with options for all tastes and gift-giving considerations. The city is home to the HQ for department store Target, which has a giant flagship downtown alongside the likes of retailers such as Macy’s and Saks Off Fifth. Thrifty shoppers will find an assortment of retailers and homegrown makers in boutiques and holiday pop-ups. And, of course, just a few minutes drive from downtown Minneapolis is the Mall of America in Bloomington, Minnesota. It’s the largest mall in the United States (in terms of number of stores and total floor area) and boasts more than 500 shops and department stores as well as Nickelodeon Universe, Sea Life Minnesota Aquarium, The Lego Store, American Girl, and tons of other family-oriented activities.

New York, New York

Christmas shopping in New York

The streets of New York are ideal for urban Yuletide outings. From admiring the seasonal window displays at the major department stores to skating beneath the giant Christmas tree at Rockefeller Center, Manhattan glistens with glitz with plenty to experience between browsing the racks and aisles of its many shops. The city’s outer boroughs do not disappoint during this time of
year either. The craftier concerns of Brooklyn, such as Williamsburg, offer a wealth of independently minded purchases from artisans and artists, while diverse Queens yields a bounty of nicely priced handmade, vintage, and seasonal items at venues such as Astoria Market and House of Holiday (New York’s largest Christmas store). Need more New York area shopping options? Woodbury Common Premium Outlets is only about an hour away upstate and New Jersey’s upscale The Mall at Short Hills is even nearer.

Portland, Oregon


One key reason to keep Portland in mind for your next shopping expedition is that the city has no sales tax. More than that though, it’s an affordable and friendly city with a good mix of globally recognized retailers and lots of local makers and brands. If you’re looking for sportswear, outdoor clothing, and related gear at a discount, Portland’s is definitely the place to go, as it boasts a Columbia Sportswear outlet store, a Nike Factory Store, and many others. And if all that shopping has made you thirsty, there’s a lot of locally brewed beer too! So whether that adds up to a drink or two along the way of a shopping trip or the chance to buy brilliant presents for the craft beer lover in your life, you’ll be in just the right place.

Got a long gift list, but need to squeeze in a quick vacay as well? Why not kill two birds with one stone and plan a trip to one of these cities?

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About the author

Chris Osburn

Chris Osburn is a freelance writer, photographer, consultant, and curator and the driving force behind the long running and award winning blog, Originally from the American Deep South, Chris has lived and worked all over the world and has called London home since 2001.

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