How to Spend the Perfect 3-Day Weekend in Kenosha, Wisconsin
Are you looking for a Midwest destination that offers lakefront charm, downtown vibes, and a delicious food scene? Look no further than Kenosha, Wisconsin, located just 90 minutes north of Chicago.
As a lifelong Wisconsinite, I was pleasantly surprised to find that this lakefront city has everything needed for a perfect getaway – fun shopping, great dining, amazing beaches – making a weekend in Kenosha a great road trip option.
Sam and I visited Kenosha on a trip hosted by Visit Kenosha during the summer months and loved every second. We chatted with lifelong locals who shared so much pride for the city, explored the many museums, and spent hours walking along the paths and waterfront trails.
Continue reading for the perfect 3-day Kenosha weekend itinerary, and start planning your next Wisconsin adventure today!
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Planning for Your Kenosha Weekend Getaway:
How to Get to Kenosha
Kenosha is a great Wisconsin road trip destination and is easily accessed via I-94/I-41. The city also has a Metra station that can transport visitors to and from Chicago.
If you are flying to the area, Milwaukee Mitchell International Airport (MKE) or the Chicago-area Airports (Chicago O’Hare (ORD) and Chicago Midway (MDW)) are your best options and offer frequent daily flights from many cities.
Regardless of whether you drive or fly to Kenosha, I highly recommend a car for your weekend in this city. While the downtown area is very walkable, a lot of the outdoor spots require a drive.
Where to Stay in Kenosha
Kenosha has every type of lodging option from standard hotels to boutique stays. You can determine the best option for you based on your budget, ideal hotel location, and size of your travel party.
I enjoyed a hosted stay at the historic The Stella Hotel & Ballroom during my weekend in Kenosha and I highly recommend booking a room here during your visit. The hotel is a former Elk’s Club and has been beautifully renovated, is very reasonably priced, and is within walking distance of Downtown Kenosha.
The Stella Hotel has a grab-and-go coffee shop, a full-service restaurant, and rooftop bar. It’s also a very popular venue for weddings.
What to Pack for a Weekend in Kenosha
Make sure you check the weather before packing for your weekend getaway as Wisconsin weather can be 90 degrees one day and 60 degrees the next. Aside from your everyday clothes, here are additional essentials for your Kenosha weekend:
– Camera – I love this mirrorless camera along with my phone for photos
– Swimsuit
– Rain Jacket
– Comfy Walking Shoes – I wear these Brooks Adrenaline for a comfy and casual option, or these very comfy Blundstone Boots for a more dressed-up look
– Small bills for the Kenosha Streetcar
Guide to the Best Weekend in Kenosha:
Day 1
Dinner at India Masala House
5745 75th St, Kenosha, WI 53142
Start your trip to Kenosha off on the right foot with a delicious meal at India Masala House. Located in an unassuming strip mall, the restaurant features a large menu full of Indian specialties like curries and tandoori options, a full bar, and delicious dessert choices.
Sam and I ordered the butter chicken, chicken tikka masala, and a side of garlic naan – and devoured it all!
If Indian cuisine is not for your tastebuds, consider 1844 Table & Mash (located in The Stella) or Kenosha Brewing Co.
Evening Walk at Simmons Island Park & Beach
5001 4th Avenue, Kenosha, WI 53140
Simmons Island is one of my favorite spots in Kenosha – home to a beautiful beach area, great waterfront walking paths, and two historic lighthouses. It’s also popular among both locals and visitors so there’s always something fun happening on the island (technically a peninsula).
Bonfire at Kenosha Beach House
5001 Simmons Island Rd, Kenosha, WI 53140
After enjoying the beautiful sights from Simmons Island, head to the Kenosha Beach house for a bonfire on the beach every Friday night through October 31, 2025. Toast s’mores at one of several small bonfires located on the beach while listening to kid-friendly music and enjoying great conversation with friends and family. Later in the evening you can gather around a giant bonfire in front of the Beach House.
Those over 21 can also enjoy adult beverages in the beer garden, where there’s also a bonfire.
➡️ Read Next: Top 13 Things to Do in Kenosha
Day 2
Breakfast at The Daily Dose
6010 40th Ave, Kenosha, WI 53142
Look no further than The Daily Dose Cafe to fuel your morning. Serving delicious egg-based dishes, paninis, frittatas, french toast, and more, you will leave the table stuffed for hours. Of course, The Daily Dose also serves a delicious offering of coffee beverages, juices, and smoothies.
Arrive early for breakfast, especially on weekend mornings and when the weather is cooler. The inside of the diner is very small with a few counter stools and just a couple of booths. During the summer months, patio dining is an option providing quite a bit more seating.
The Daily Dose is also open for lunch. The cafe is closed on Sundays.
Kenosha HarborMarket
2nd Ave &, 56th St, Kenosha, WI 53140
If you’re visiting on a Saturday during the summer and fall months (May through October), a stop at the Kenosha HarborMarket is a must. The market takes place by the museums, Harbor Park, and the Southport Marina, and features more than 100 vendors each Saturday.
I love the mix of small businesses that partake in the market. You’ll find everything from small jewelers and woodworkers to cheesemakers and kombucha specialists. If you plan your visit right, you can enjoy breakfast and lunch at the market.
From The Stella Hotel, I hopped on the Kenosha Streetcar which picks up just a block from the hotel and drops off right next to the market.
The fare for the streetcar is $1 per loop for adults 13+ or $0.50 for those age 5-12. It’s a really fun way to experience the area.
There is also a Winter HarborMarket held indoors during the winter months, although I have not been.
➡️ Check Rates at The Stella Hotel
Lunch at Coopers Uptown
2401 60th St, Kenosha, WI 53140
Head to Coopers Uptown for a cozy cafe lunch featuring soups, sandwiches, salads, and delicious ice cream desserts. The cafe is nestled within the store, providing you the perfect excuse to do a little shopping while you wait for a table or after you eat.
I enjoyed a tasty grilled cheese sandwich and Sam devoured the Sweets & Beets Quinoa salad. The cafe is very cute, the service fast, and the food delicious.
Of course, afterwards I had to check out the items in the shop. They sell everything from home decor items and Kenosha-branded sweatshirts to cigars and grill-out goods. I even found a book to help prepare your affairs once you die – that was unexpected!
The cafe serves food daily until 2pm, but the shop is open until 5pm weekdays and 4pm weekends.
Hawthorn Hollow Nature Sanctuary and Arboretum
880 Green Bay Rd, Kenosha, WI 53144
In my opinion, Hawthorn Hollow Nature Sanctuary and Arboretum is the most wonderfully unexpected place in Kenosha. This 90-acre nature escape includes an arboretum, hiking trails, historic buildings, and so much more, all just a short drive from downtown Kenosha.
I took a golf cart tour of the property with the executive director, TJ Leveque whose love for the nature sanctuary shined through his excitement talking about upcoming projects, spotting a new batch of mushrooms, and showcasing his staff members.
I spent just under two hours exploring the property, but easily could have spent an entire day. There are just about 5 miles of hiking trails to explore, along with a fruit and veggie farm and the arboretum.
Hawthorn Hollow is free to visit and is open daily from March 1st through December 23rd. It is closed for the winter from December 24th through February 28th/29th.
Dinner at Waterfront Warehouse
3322 Sheridan Rd, Kenosha, WI 53140
If you’re looking for a spot everyone in your group will enjoy, look no further than Waterfront Warehouse. This warehouse-style location is a fun spot for lunch and dinner with a HUGE menu. They even have a dedicated gluten-free menu Sam ordered from.
Since it’s a rare occasion that I get regular pasta these days, I ordered the rigatoni and Sam had another salad, this time with quinoa.
And when I saw the dessert menu had a s’mores flatbread on it, I did not hesitate to put in an order. It did not disappoint.
Rooftop Drinks at Crow’s Nest Rooftop Bar
5706 8th Ave, Kenosha, WI 53140
Grab post-dinner drinks on the top floor of The Stella Hotel at Crow’s Nest Rooftop Bar. Order a beer or cocktail from the bar and then grab a seat with a view while enjoying the sunset or city night lights.
It’s the perfect way to end the day, especially if you’re staying at The Stella.
➡️ Check Rates at The Stella Hotel
Day 3
Breakfast at The Buzz Cafe
5621 6th Ave, Kenosha, WI 53140
The Buzz Cafe is a great morning hangout spot offering coffee, smoothies, and a few breakfast items. In the afternoon, stop by for a huge selection of wines and beers.
Grab breakfast from 7-11am, including a variety of bagel and wrap options and a large case of baked goods to choose from. I also enjoyed a delicious berry smoothie.
The space is very welcoming and is a great option for a morning meeting with friends or as a remote work location.
Morning Hike at Kenosha Sand Dunes
8228 7th Ave, Pleasant Prairie, WI 53158
Part of the northernmost portion of the Chiwaukee Prairie State Natural Area, the Kenosha Sand Dunes is an open area of dunes along Lake Michigan.
You can park at Southport Park and take a short path to the start of the 2-mile loop trail through the dunes and along Lake Michigan. Depending on the season, expect to see various flowers, birds, and gorgeous views of Lake Michigan.
Please keep in mind that most of the trail is sand and can be difficult to walk through in portions. Additionally, I found the trail to be quite remote. I never felt unsafe and absolutely recommend the hike, but as always, make sure you’re aware of your surroundings.
Southport Light Station Museum & Lighthouse
5117 4th Ave, Kenosha, WI 53140
Kenosha is fortunate to have two lighthouses – the Southport (Kenosha) Lighthouse and the North Pier Lighthouse – that contribute to the maritime history of the city. While the North Pier Lighthouse is the famous red one showcased frequently in photos of Kenosha, the Southport Lighthouse is the one you can tour.
There’s a free museum in the keeper’s residence featuring images, artifacts, and stories of Kenosha as an important harbor during the 19th century.
For $10 per adult ($8 per child age 8-11), you can climb the 72-step spiral staircase to the top of the Southport Lighthouse. I love going to the top of lighthouses to see how far in the distance I can recognize a spot.
Lunch at Boat House Dockside Pub & Eatery
4917 7th Ave, Kenosha, WI 53140
An awesome spot for lakeside dining in Kenosha, Dockside Pub and Eatery offers both great views and delicious food. Grab a spot inside next to the windows, or sit on the deck if the weather is nice.
The Ocean Waves are a must for an appetizer. They are fresh cut potato chips with parmesan cheese and a drizzle of balsamic and oh my goodness are they delicious. For entrees I had a delicious Nashville Hot Chicken and Sam had one of the many gluten free salad options.
There’s a small parking lot behind the restaurant, but if it’s full there’s plenty of free street parking across the street.
Hike at Richard Bong State Recreation Area
26313 Burlington Rd, Kansasville, WI 53139
A beautiful outdoor spot that I didn’t get to spend nearly enough time at is Richard Bong State Recreation Area. This SRA offers almost 30 miles of trail, campsites, and a lake popular for fishing and birding.
Since we were short on time, Sam and I walked the 0.7-mile Visitor Center Nature Trail which is a beautiful path with interactive stations for kids to learn more about the outdoors. I’m already planning my next trip back to explore one of the longer trail options.
A Wisconsin vehicle admission sticker or $5 day pass is required for entrance.
➡️ Read Next: Top 13 Things to Do in Kenosha
Conclusion
I hope this itinerary helps you plan the perfect weekend in Kenosha. This city has so much to offer for every visitor, and you’ll certainly need much more than a 3-day weekend to see it all.
If you’re looking for more things to do in Kenosha, just out my guide on the Top 13 Things to Do in Kenosha and as always, let me know if you have any questions.
