Winter is the perfect time for an Okoboji Couples get away!  Winter is a beautiful and much slower paced time to visit the Iowa Great Lakes while still finding plenty to keep you as busy as you want to be.

 Rest & Relax

Oakwood Inn

Winter is a GREAT time to head to Okoboji to relax, refresh and reconnect!  For an amazing couples getaway that includes a breakfast you won't soon forget check out the adults only Oakwood Inn Bed and Breakfast.  This property recently was given Select Registry status which is on of the highest honors for independent and boutique properties.  Other cozy winter stays with dining on property include: The Inn, which was brand new in 2019, and houses The Beach Club for amazing food and craft cocktails; the newly remodeled Arrowwood Resort which houses Minerva's restaurant; Bridges Bay Resort where you can dine at The Water's Edge Grille; and Village West Resort and the Main Event Bar and Eatery.  For a traditional hotel and a great night sleep there is: Okoboji Inn and Suites,The Roadway Inn, AmericInn, Ramada, or Super 8.

The Inn

The Inn Hotel

 EAT and Drink


Beach Club Lounge


Okoboji has no shortage of amazing places to eat or sip on a cocktail all season long. Looking for a special occasion meal you can't go wrong at The Beach Club LoungeMinerva's, The Outrigger, Tweeter's, or The Water's Edge Grille.  For casual dinning while watching your favorite college or pro team play try Tweeter'sThe Hutt, The Gardens ,The Ritz, Captain's or Nautical.  For a cozy meal where good conversation can abound check out The Dry Dock, Snappers, or The Main Event at Village West. If its Pizza you are craving you MUST check out Pub 19 at Okoboji View golf course or the extensive flatbread menu at opens in a new windowThe Water's Edge Grille.  Be sure to stop at West O and Okoboji Brewing Company, for locally brewed craft beer, come in the afternoon and you may be able to get a brewery tour. If you are here on a Tuesday you will want to try all you can eat pasta night at Minerva's. If you would rather stay in the cozy quiet of your hotel room you can have Jimmy John's, Godfather's, or Pizza Ranch deliver right to your door.





Pub 19 Bar and Grill


The Outrigger


Ice Fish

Why yes you can enjoy the Lake on the winter!  From ice fishing to ice skating its so fun to walk and play in the water we boat and swim in all summer!

Stop by an area bait shop before you head out on the ice for an afternoon of fishing. The Hook Up and Oak Hilll Outdoor in Milford can offer great tips, sell you any bait and supplies you need, and give helpful advice of locations to avoid to stay safe.  All of our opens in a new windowarea bait shops can give you helpful tips & advice on where to find the hot bite!  If you’d like more guidance, it’s well worth the money to hire a fishing guide to take you out for a few hours.  Your guide will have all the supplies you need and make sure you have a day to remember!

If you’d like to try ice skating, we’ve got you covered! The Fish House at Okoboji Boat Works in Okoboji rents ice skates and clears an outdoor rink on West Lake Okoboji!  When you need to warm up, step inside and enjoy a beverage at their bar, or drop a line – it is the largest winter fish house in Okoboji!  The Boji Bay Ice Arena is a great destination for indoor ice skating.  The indoor arena is filled with local hockey teams most weekdays, but everyone can get on the ice during open skate on Friday & Saturday nights!  Skate rentals are available.

Ice skate


Cross Country Ski

Winter is a quiet and picturesque time to hit the multi-use trail system that winds its way through the Iowa Great Lakes. With over 40 miles of paved trails there are lots of places to see and explore via fat-tire bikes, snowmobile (designated trails only), snowshoes, cross country skis, or just lace up the boots and take a walk.   The "spine" of the system is a 14-mile trail through the heart of the Iowa Great Lakes region, connecting to the spine trail are several other shorter trails to explore including the Kenue Park Trail, Arnolds Park City Trail and the Spirit Lake City Trail.  The trail also loops around the East and West sides of Big Spirit Lake where it joins the Loon Lake Trail at Mini-Wakan State Park.   If you are looking for a winter hike off the beaten path check out the nature trail at Kettleson Hogsback Wildlife Area, which has groomed cross country ski trails, The Interpretive Trail at Gull point, or Horseshoe bend recreation area south of Milford.  opens in a new windowBrooks Golf Course also offers groomed cross country ski trails from the clubhouse to the opens in a new windowNature Center.

Winter trail


Okoboji Classic Cars

History buff or not, winter is the perfect time to visit Okoboji's many and varied museums.  Our local museums can help take you on a trip through time to learn about how this place came to be! Start at the Iowa Great Lakes Maritime Museum located in the year-round Iowa Welcome Center and gift shop.  The friendly folks here can help point you in the direction of anything going on in Okoboji!  The Maritime Museum itself houses an impressive collection of antique wooden boats, and maritime history. The Arnolds Park Funhouse Museum is housed in the same building with so much fun memorabilia including the wooden slide, barrel, and sugar bowl. I promise if you take one ride down the slide you will want to take another!  While here you can also swing through the Iowa Rock 'N Roll museum which preserves the legacy of Rock 'N Roll in Iowa We are not exaggerating when we say you could spend ALL DAY at the Clark Museum in Milford.  This museum features thousands of historic photos of the area as well as artifacts from restaurants, the amusement park and so much more.  There is also a historic reading area which includes information on darn-near every county in Iowa!  You will most definitely NOT want to miss the Okoboji Classic Cars Museum, which showcases a rotating inventory of restored classic cars amidst a backdrop of floor to ceiling murals by artist Jack Rees.  Even if you are not a classic car lover you will be WOWED by Okoboji Classic Cars!  The guided tour they take you on through the building enhances your experience, and makes it fun for all ages!

While not a museum, you should also make time to visit the Polaris Indian Motorcycle Experience Center in Spirit Lake. Take a guided tour of their assembly floor led by staff who work in a variety of capacities. Following the tour, you can view artifacts on display in the new reception / exhibit area. Tours last approximately 1 hour, and are best in the morning, but be sure to call in advance to make a reservation - this is a working factory and they need to know you're coming. (712-336-6955)



Iowa Rock 'n Roll Museum

Indoor Entertainment


Art Center exhibit

Pearson Lakes Art Center

If you're looking for more indoor fun, there is no shortage. Channel your inner artist by strolling through the Pearson Lakes Art Center.  While there check out their class listing and work on your own artist skills.  Speaking of art you can also paint your own masterpiece at the opens in a new windowKurio Castle Pottery Painting Palace in downtown Spirit Lake. You might also enjoy a step-by-step guided painting class at opens in a new windowCreative Spirits.  Next, stop at the Dickinson County Nature Center where environmental learning abounds! There is always something to see and do, whether it be visiting an exhibit or playing with the permanent displays. Plus, it's all free! You can even borrow a set of snowshoes and walk the trails.

The Throwing Post, Okoboji's hot new attraction, invites you to come throw some axes.  Guaranteed to be easier and way more fun than you think it possible!

Catch a movie at  Great Lakes Cinema 7 which has multiple screens and a popular selection of the newest movies! The Milford Pioneer Theater has added a second theater which boasts all leather recliner seating, highlights the newest movies and has online booking where you can even pick the seat you want.  Both have comfortable seating, buttery popcorn, and a wide variety of delicious treats!

Corner Lanes bowling Alley in Spirit Lake has been recently renovated, has delicious food, drinks, music and of course bowling. 

Riddle me That is the perfect place to work on your communication skills as you work together to solve a mystery to  ESCAPE from a room full of puzzles and clues. There are no pictures of the rooms, as we do not want to give away any hints to help solve the riddle, but each of their rooms are different and difficult to solve. You must work together to get out in time! Make your reservations in advance to include this fun (and challenging) stop on your trip.


Okoboji Shopping


No trip to Okoboji is complete without doing some shopping!  The stores will be all decked out with winter and maybe a hint of spring housewares, clothing and accessories!  Be sure to check out Homeology and Elements right in the center of it all in Arnolds Park.  Next head up toward Spirit Lake stopping at West Boutique in Okoboji, on the hill by Okoboji Boat Works, with a great selection of clothing and shoes.  The next stop is Mary’s, where you can shop home decor, clothing, a huge selection of kitchenware and gourmet food perfect for entertaining.  Next is the Great Lakes Mall where you will you will find The Look, Wild Child, Fashion Formula, Interiors, and opens in a new windowSpirit Lake Silver and Gold. If you are more into antique shopping there is no shortage of antique stores in Okoboji.  Be sure to check out Antiques Etc., Spirit Lake Antique Mall, (both open March - December)and Timeless Consignments (open year round).  The stop no one should miss on a trip to Okoboji is The Three Sons in downtown Milford.  This is your spot for official University of Okoboji gear!  Proof that you're working towards your degree in fun!

The Three Sons

Okoboji Treasure Shopping

Antiques Etc.

Day trip

Round Lake Winery

Looking to branch out for a day?   Start the day off with a late breakfast at The Hutt or Dry Dock (weekend breakfast only) and then take off for Round Lake Vineyards in Round Lake in Minnesota.  The Vineyard and grounds are beautiful and the wine and food are amazing too.  Hop back in the car and head east to the Little Swan Lake Winery where you will find great musical entertainment most weekends.  For dinner make your way back to Okoboji for many great options.

As always if you have any questions or need other recommendations please call us at 1-800-270-2574. We would love to help you plan your Winter getaway to Okoboji!


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Click here to learn more about our "Top Winter Activities!"

Winter Park scene