Ask 100 people what a vacation in Minnesota would look like, and at least 75 would paint you a picture of a lakeside retreat, likely somewhere in the north woods. For those looking to explore something different, Winona is a great example of what southeastern Minnesota looks like – limestone bluffs rising up from the river, eagles soaring overhead as visions of Huckleberry Finn perched atop his raft are conjured up. Known in some circles as the stained glass capital of the United States, Winona’s natural beauty (such as the Sugar Loaf rising more than 500 feet above Lake Winona) serves as the inspiration for artisans of all types. Long-time resident and business owner J.R. Watkins famously coined the phrase “money back guarantee,” so you’ve got nothing to lose if you steal away here for a weekend.

Getting There

Located approximately 2.5 hours southeast of the Twin Cities metro area, you have several different picturesque options to arrive at your destination. Cruising down US-52 will provide your gateway to the limestone bluff region of Minnesota via Rochester (with a turn east on I-90), and includes quite a few lunch options along the way. To follow the course of the Mississippi River, head east on 94 to US-10 (and enter into Wisconsin), then head south on WI-35. You will cross back into Minnesota just outside of Winona, but the chance to “travel the river” is well worth it. Your third major option retraces some of the path along WI-35, but spends the majority of the trip on US-61, occasionally keeping the river in sight, but often swinging a bit further away as it traces the natural topography of the Minnesota side.


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Riverport Inn & Suites
900 Bruski Drive
Winona, MN 5598
(507) 452-0606

Price: from $99/night

For the traveler familiar with hotel-style amenities, Riverport offers 106 rooms, including several special themed rooms — sleep in a drive in if you choose and try a ’57 or ’59 Chevy bed, complete with large screen TV in front of you. Brewski’s Pub & Grill is a great place to eat or take in the big game on site. Settle in after a long day in the full-sized pool or whirlpool. Rent a room with an in-suite wet bar or whirlpool for a more private setting, or choose a room with a view of the bluffs and the towering Sugar Loaf above you. Even if you decide to stay elsewhere, Brewski’s is a worth a stop during your stay.

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Village House Inn
72 College Road
Winona, MN 55987
(888) 450-4322

Price: from $90 a night

Offering four guest rooms, each with its own theme and distinctive accommodations, guests may choose the room most fitting of their ideal vacation, or rent the entire house for an extended family getaway. Located in a quiet neighborhood just minutes from both the river and historic downtown district, the Village House Inn offers modern conveniences — whole-house WiFi, coffee and tea from the Keurig at any time — in a historic setting. Special vacation packages are available in conjunction with several local attractions and events — the Great River Shakespeare Festival, or plan your own weekend with the Great River Road Wine Trail package — as well as themed packages including a golfer’s getaway or the River City Romance package.

RelatedFlying Carp Found In Winona

What to Do

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Trester Trolley Tours
(507) 429-9101

Price: $10 adults/$5 children/free children 5 and younger

Departing Saturdays at 10 a.m. from the Holiday Inn Express, the Trester Trolley is a labor of love envisioned by Don Trester and carried on after his passing by his friend and long-time Winona resident Clarence Russell. The standard tour is 28 miles long, narrated by Clarence throughout a 90-minute trip along some of the best sights and sounds that the city has to offer. Chartered trips are also available. Call ahead for reservations to ensure you and your family get a seat.

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Lake Park Lodge Rentals
Main Street
Winona, MN 55987
(507) 457-8258

Price: free

In keeping with the state-wide theme of getting outside and exploring all of the recreational opportunities that this great state has to offer, the Winona Park & Rec department has decided to offer a unique program – free watercraft and bike rentals. Available from 4 p.m. to 8 p.m. during the week, and from 1 p.m. to 6 p.m. on Saturdays, the Park & Rec department offers free use of a wide variety of water-based options including canoes, kayaks and standing paddle boards as well as life jackets and paddles, and bikes with helmets from Lake Park Lodge, which is located at the end of Main Street on East Lake. The rentals are also available for an extra hour on Wednesday evenings until 9 p.m., offering an interesting way to enjoy the evening sounds of the Municipal Band from the river. Children 16 and 17 years old will need a guardian’s signature on the waiver form to take advantage of this great program, and anyone younger than 16 will need both a guardian’s signature and to be accompanied by that same person while they are on the water.


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Blooming Grounds Coffee House
50 E. 3rd Street
Winona, MN 55987
(507) 474-6551

Mixing the modern trend for a great cup of coffee with the comfort of home-baked goods like your mother would make, this place just can’t be beat for a warm cup of joe and a quick bite. While coffee is in the name, delicious summer staples including smoothies and frappes offer a cold alternative while taking in the sweet smell of fresh-baked treats. A full meal menu is available, as is catering for corporate events and family gatherings. Stop by for a great start to your day about town, or settle in for a gourmet pizza or panini as you unwind from a long day of exploring the town. Not only is Blooming Grounds a great place to catch a tasty drink, but the meals really do deserve their own place in the name.

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Lakeview Drive Inn
610 E. Sarnia Street
Winona, MN 55987
(507) 454-3723

Founded in 1938, the Lakeview Drive Inn is Winona’s oldest restaurant – and likely one of the most unique. Featuring car-side food service and the closely guarded secret recipe root beer, this is one stop sure to take you back to simpler times without having to lower your expectations, as both the service and the fresh-cooked food are sure to please. The famed beverage is also available to go, but there is just something about a nice frosty mug on a summer day that is best experienced how founder Emil Berzinski intended it – sitting in your car, surrounded by other patrons soaking in the atmosphere.

Related: Road Trip Rules

610 East Sarnia St
Winona, MN 55987

Rich Rein has been featured in Midwest Outdoors and Outdoors Weekly magazines and has been a contributor to and He is a Minnesota transplant staying busy holding down a career as a software developer by day and a firefighter/EMT by night. His work can be found at