When you visit Portland, Maine, every sort of all-American shopping experience is within easy reach. No East Coast city can compete when it comes to the rich variety of retail expeditions that can fill your days. The city's old-time seaport shopping district is distinctly Maine, and on its outskirts, artisan wares, original art, and funky flea-market finds await. Just north of Portland, the outlet-intensive village of Freeport is home to Maine's most famous retailer, while in South Portland, Maine's largest indoor mall is a destination for on-trend apparel, electronics, and home furnishings.
The Old Port Shopping District
Portland's popular Old Port shopping district has been restored to its 19th-century splendor. With Casco Bay in view, these cobbled streets and brick Victorian buildings now house restaurants, boutiques, and specialty shops that sell everything from local handcrafts and Maine-mined tourmaline jewelry to clothing and souvenirs.
Portland-based designer Jill McGowan has spent 25 years perfecting the woman's button-down shirt, and her beloved styles are all made in the USA. Sea Bags' totes and carryalls are made from recycled sailcloth, and in the summer, you can watch the sewing team hand-stitching these sustainable and fashionable accessories. For those who still cherish traditions like sending handwritten cards and jotting in journals, Gus & Ruby Letterpress is an enchanting stationery and gift shop owned by two New England women; their eye for design gives everything they create and curate a look that is classy and fresh.
Gourmands and home chefs are in heaven here, with shops like Stonewall Kitchen, SKORDO, Vervacious, the Cabot Farmers' Annex, Dean's Sweets, and Harbor Fish Market selling delectable products. Meanwhile, Two Fat Cats Bakery turns out seasonal whoopie pies made from scratch.
On the fringes of the Old Port, away from the touristy bustle of the waterfront, you'll find a cluster of artisan shops along Middle Street. For Portlanders, these are go-to places for distinctive gifts. Don't miss Rough & Tumble, whose rugged bags, boots, shoes, and accessories are all handcrafted by skilled Mainers using Italian leathers and other fine materials. At Salt Cellar, you will find cooking seasonings like earthy white truffle sea salt, Himalayan salt lamps, and skincare products such as scrubs. It also features a vault where you can enjoy the therapeutic benefits of salt inhalation. As you mosey back toward the Old Port, pop into Fitz & Bennett Home, where the gorgeous compilation of housewares includes many products by local designers.
The Galleries in Portland's Arts District
The truly exceptional Portland Museum of Art is central to the city's Arts District, and there's no admission fee to shop the PMA Store for gifts and souvenirs during regular museum hours. From here, art enthusiasts interested in viewing and shopping for original works can hop from one gallery to the next: stop into Roux & Cyr International Fine Art Gallery to see a selection of works by painters from Maine and afar; the second-floor space at Grant Wahlquist Gallery, which hosts solo shows by contemporary artists; Abacus Gallery for handcrafted jewelry and home décor pieces; and Portland Art Gallery, where you can browse the diverse creations of more than 50 local artists. Special festivities at these and dozens of other arts spaces in the city make First Friday Art Walks, held each month in Portland, fun evenings for celebrating creativity.
The vintage game is strong at this three-story indoor flea market, which operates Friday through Sunday year-round in downtown Portland. This is not your typical dusty, jumbled antique shop: Everything here, from furnishings to art to knickknacks, is beautifully staged. Whether you're into vintage fashion and antique jewelry, vinyl, or a mid-century cone fireplace, the Portland Flea-for-All boasts a wealth of rare finds. You'll need an hour or more to see and appreciate it all. Most items are fairly priced, and this is the one shopping destination in Portland where haggling might net you a better deal.
Just four miles south of downtown Portland, the Maine Mall in South Portland is the state's largest shopping mall. You'll appreciate that it's all enclosed on rainy and wintry days in Maine, and it's a treat to find everything under one roof during the busy back-to-school and holiday shopping seasons. Fast-casual eateries or the all-you-can-eat Hometown Buffet will keep you fueled for exploring 113 stores, including Build-a-Bear Workshop, Macy's, and a rare surviving Sears. Jordan's, Maine's largest furniture store, opened a new location in July 2020, promising to be as much a spot for family entertainment as it is for test-driving couches.
Venture just over 20 minutes north of Portland to Freeport, the state's top shopping village. It's populated by dozens of factory outlet stores from well-known brands (Calvin Klein, Vineyard Vines, and Cuddledown) as well as the L.L. Bean flagship store, which is famously open 24/7, 365 days of the year. Park once, and you can spend the day strolling between well-stocked shops, picking up lobster rolls from Linda Bean's for an impromptu picnic, and taking photos of the enormous Bean Boot outside the main entrance to L.L. Bean.