A Thrifty Weekend in Winona Trip Itinerary
Grab your besties and queue up your best road trip playlist. Right off the Great River Road, there are shops to hit and secondhand items to score. We’ve put together a weekend itinerary for a weekend full of thrifting, coffee houses, and memorable bites in the heart of Winona.
Friday Evening
Arrive at CAMP EVERYDAY
The adventure starts the moment you check in at Camp Everyday. With over 74 unique sites, you can rent a cabin, camp in a tent, or roll into town in your own RV for a scenic stay in the Mississippi River Valley that’s just minutes from downtown Winona.
Dinner at 929 Beerhouse & Grill
Kickstart your weekend in Winona with craft beer and bar food classics over at 929 Beerhouse & Grill. Come as you are, dig into some crispy wings, enjoy great conversation, and ease into the weekend.
Nightcap at Two Fathoms
Pop over to downtown Winona for a nightcap at Two Fathoms Brewing. Browse their menu of original, limited release brews crafted right here in Winona. Find your new favorite beer and a comfy spot to enjoy live music the rest of the night.
SATURDAY
Breakfast at Mugby Coffee
Fuel up for the day ahead at Mugby Coffee. This drive-thru and walk-up spot brews up espresso and coffee with a curated menu of quick bites to send you on your way with a smile. With a coffee in hand, it’s time to hit some thrift and antique stores!
Treasures Under Sugar Loaf
Seated at the foot of Winona’s iconic Sugar Loaf Bluff, Treasures Under Sugar Loaf is a must-visit. Located in the historic building that was home to Bub’s Brewery, it’s easy to spend a few hours in this multi-floor wending wonder of antique home décor, collectible coins, jewelry, and other finds that range from rare to truly wild.
Paperbacks & Pieces
Paperbacks & Pieces is Winona’s oldest and largest new and used bookstore. This indie bookstore is truly a book lover’s paradise, with over 40,000 titles spanning dozens of genres on their shelves. Stop in to find your next immersive read or gifts made by local artists.
Lunch at Heirloom Seasonal Bistro
All that thrifting worked up an appetite. Head on over to Heirloom Seasonal Bistro in the heart of downtown Winona. Just blocks from the Mississippi River, this family-owned restaurant boasts an ever-changing menu of farm-to-table dishes made with locally sourced ingredients. The smash burger is a fan favorite, and the scratch made pasta pairs perfectly with a crisp glass of wine from Elmaro Vineyard just across the river in Trempealeau, WI.
Chapter 2 Books
After lunch, Chapter 2 Books is the perfect next stop on your thrifting tour. This beloved bookstore is filled with used books, DVDs, and records ready for their second lease on life. Founded by Winona native, Daryl Lanz, and “guarded” by the sweetest shop cat, Chapter 2 Books is a haven for analog media enthusiasts with an evolving stock of popular media, throwback comics, and rare collectibles.
Heart’s Desire
Soup and dip mixes, fishing gear, jewelry, stationery — find it all and then some at Heart’s Desire. Aptly named, this charming store has just about anything and everything. Whatever your heart desires, there’s a good chance you’ll find it right in the heart of Winona.
Mélange Resale & Boutique
Stroll on over to Mélange Resale & Boutique. You’ll find racks filled with new and pre-loved, size-inclusive clothing that blends current styles with an eclectic flare. Find an outfit for your next wild night out or tasteful décor that comes with a story of its own.
Grace Place
Right next door to Mélange is Grace Place. Peruse second-hand household items and clothing among an eclectic mix of items seeking their second lease on life. Living up to its name, Grace Place is filled with unique finds and benefits families in the community.
Head Back to Camp Everyday
Drop off all your latest finds and take a pre-dinner dip in the outdoor pool. Once you’re feeling refreshed and ready for some excitement, head back to downtown Winona for a night on the town.
Happy Hour at The Lafayette
Kick off the night with some seriously wild handcrafted cocktails during happy hour at The Lafayette. How wild can a drink get? Order Neptune’s Wrath and you’ll see. Just be sure to keep anything flammable a safe distance from your drink.
Dinner at Muddled Thyme
Follow the mouthwatering smell of brick oven-fired pizza over to Muddled Thyme. Start off with one of their signature drinks or a Winona Old Fashioned. If you’re open to it, ask the mixologists what would pair the best with a savory order of apps and the gourmet pizza of your choosing.
Night Cap at No Name Bar
Dinner may be done, but the night is far from over. Walk on over to No Name Bar where live music and carefully curated cocktails await. Browse local art, play your heart out at pinball, or cozy up on the couch to toast your last night in Winona.
SUNDAY
Now’s the hard part…leaving. After you’ve packed up your site, loaded all your new treasures into the car, and checked out of Camp Everyday, you can perk back up with coffee and breakfast at Blue Heron Coffeehouse on your way out of town. The menu changes with the seasons, but the bakery case is always overflowing with fresh goodies perfect for any weather.
If you’re still in the mood to linger, commemorate this fun weekend with a picture by the Winona Letters near the Winona Visitor Center.
