Step into a world of whimsical wonder in this picturesque river town as we explore the cutest shops in Winona, Minnesota.

Prepare to be enchanted as we unveil the hidden gems nestled amidst its charming streets. From delightful boutiques to cozy cafes, Winona boasts a collection of the top 5 cutest shops that will steal your heart. Join us on this captivating journey as we showcase the must-visit destinations where timeless elegance meets modern allure. Whether you’re a local seeking a new shopping haven or a traveler seeking an authentic experience, these enchanting shops are guaranteed to leave you spellbound. Get ready to explore the captivating charm of Winona, Minnesota, and discover the irresistible allure that awaits!

Are you looking for fun, quirky and cute shopping in Winona, Minnesota? Look no further! Winona, Minnesota is a hidden gem brimming with fun, quirky, and undeniably cute shops just waiting to be explored. Whether you’re a local seeking a new shopping adventure or a traveler passing through, this vibrant town has something to delight everyone. From charming boutiques filled with whimsical treasures to trendy stores showcasing the latest fashion finds, Winona offers a shopping experience that is as unique as it is captivating. Get ready to indulge your love for all things cute as we embark on a journey to uncover the most charming and unforgettable shopping destinations in Winona, Minnesota.

Do you ever find yourself wondering…is Minnesota a good place to live? Read our pros and cons post from a local and find out now:

Cutest Shops in Winona, Minnesota

Cutest Shops in Winona Minnesota
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1. ORNO Gift + Home
78 E 3rd St, Winona, MN 55987

My first shopping stop is usually Orno…it’s an adorable store full of cute things located right in the heart of downtown Winona. 

Orno is the vision of owner and jewelry artist Jovy Rockey. Their focus is on promoting high-quality work made by independent artists. They provide a unique selection of gifts, home decor, crystals, and clean beauty products while offering a brick & mortar shopping experience that delights all the senses.

At this adorable shop you’ll find the work of over 80 independent and fair trade artists, designers, and makers which include: jewelry, ceramics, art prints, screen printed goods, natural body care, framed art, hand-blown and stained glass, home decor, textile art, greeting cards, accessories and more. 

I seriously love Orno and could easily spend all of my time…and all of my money…here. But I need to save some cash, because I’m on a treasure hunt…and where better to go next than Treasures Under Sugar Loaf.

Cutest Shops in Winona Minnesota
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2. Treasures Under Sugar Loaf
1023 Sugar Loaf Rd, Winona, MN 55987

Ok, y’all, this antique store is literally under Sugar Loaf, which is a bluff on the Mississippi River topped by a rock pinnacle, which overlooks the city of Winona. It’s pretty iconic to folks from around here. 

Native American legend says that the mountain is actually the cap of Chief Wapasha I who was transformed into stone upon his passing. In 1862, Peter Bub founded the Sugar Loaf Brewery, also known as Bub’s Brewery. Peter’s brewery complex involved storing the brew in caves dug into the bluff. His brewery building has now been converted into a sprawling antique mall called Treasures Under Sugar Loaf.

Treasures is proud to be a family-owned business and a part of the close-knit community of Winona. They feature over 60 knowledgeable antiques and collectibles dealers who supply a wide variety of unique vintage items that are spread all throughout their massive three-story building. New items arrive daily, so you will always find something different at Treasures Under Sugar Loaf!

Cutest Shops in Winona Minnesota
How adorable is this doggo? Kieva loves to help customers find their next pawsitively awesome book!

3. Paperbacks and Pieces
429 Mankato Ave, Winona, MN 55987

Just a short drive from down Mankato Avenue you’ll find Winona’s oldest and largest used bookstore. Paperbacks and pieces was established in 1977, and is beloved by readers in Winona.

Their focus is on books, and they have just over 40,000 titles on the shelves. What’s neat is that about 90% of the store is gently used books…which they sell at 50% of the cover price, so you can really find some great deals. 

The store is called “Paperbacks and Pieces”, and the “pieces” in their name refers to a selection of cute gifts and merchandise. You’ll find purses and wallets, jewelry, candles, cards and postcards. There’s even a fun Puzzle Exchange by the front door. Puzzles are brought in and exchanged for free. They do not count the pieces or monitor who takes what…it’s just a community courtesy.

Cutest Shops in Winona Minnesota
Look for this sign and follow the steps downstairs…a vintage world of charms awaits!

4. A-Z Collectibles
152 Main St, Winona, MN 55987

Speaking of community, A-Z Collectibles has been selling memories since 1993 in downtown Winona. This is Jack’s favorite antique store in Winona. The basement shop is packed to the gills with stuff…and it’s all quite affordable.

This store might not be as cute as my other recommendations, but if you don’t mind digging for your vintage finds, you’re sure to find something fun and funky!

A-Z sells vintage kitchen items, beautiful glassware, and older pottery. They have an ever-changing selection of hip used clothing – coats & jackets, unusual men’s ties and cute vintage threads. You’ll also find vintage records, books, books and more books. Did I mention how much Winonans love to read?

I like visiting A-Z for their vintage clothes…sometimes you can find some really cute gems. Speaking of cute, my final pick couldn’t be more different…but it’s located just a few steps away. 

Cutest Shops in Winona Minnesota
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5. Loft on THIRD
69 W 3rd St, Winona, MN 55987

Loft on Third is a fun and energetic women’s clothing boutique offering unique pieces to add to your wardrobe. Everything they sell can be described in one word: adorable!

Lynne and Rachel, the lovely ladies behind Loft, take pride in offering the highest quality, most unique merchandise on the market today.

If you’re looking for cute tops, sweatshirts, graphic tees, dressers and rompers, bottoms, basics, jewelry and accessories, shoes and more…chances are Loft on Third has something that will catch your eye.

Loft put lots of love and careful attention into each item they offer customers. This is affordable fashion for all…and I know you’ll love visiting Loft as much as I do. When you’re done shopping head across the street to Blooming Grounds Coffee House for one of the best lattes you’ll ever taste!


In conclusion, the charming town of Winona, Minnesota, has proven itself to be a haven for those seeking a delightful shopping experience. Our exploration of the top 5 cutest shops has revealed a world of enchantment and allure, where every corner holds a unique treasure waiting to be discovered. Whether you’re captivated by the timeless elegance of vintage boutiques or drawn to the modern appeal of trendy stores, Winona offers a delightful blend of old-world charm and contemporary allure. From locally crafted goods to artisanal treats, each shop adds its own touch of magic to the vibrant tapestry of this enchanting town. So, come along and immerse yourself in the captivating charm of Winona, where the cutest shops await to enchant and inspire visitors from near and far.

What did you think of our list of the cutest shops in Winona, Minnesota? Which ones do you want to visit? Let us know in the comments.

Have a super day!

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About the Authors
Jack and Kitty Norton are Emmy Award winning travel experts. They have spent a lifetime on the road: as traveling musicians, documentary filmmakers and television producers. They now focus on writing for their travel blog ( and making fun videos for their YouTube channel. Jack and Kitty offer travelers fun and quirky things to do in Minnesota, the Midwest and beyond. High school sweethearts turned married soulmates, the couple lives in the small college town of Winona, Minnesota and would love to have you over for some hotdish.

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