4 Epic Summer Weekend Itineraries Around Greater Madison, WI

Madison’s got way more going on than just the Capitol and the Terrace chairs (though, let’s be honest, we love those too). If you’re looking to squeeze the most out of your weekends this summer, whether you're local or visiting, we’ve rounded up four adventure-packed Friday–Sunday itineraries.

They're filled with low-key gems, foodie finds, outdoor hangs, and a few spots you might not have heard about yet. Let’s go!

1. Lake Vibes + Hidden Breweries Weekend

Friday:

• Kick things off at Lakeside St Coffee House, a chill spot with big character right off Lake Monona.
• Then hit up Orchard in Verona for small-batch hard ciders you won't find just anywhere. Grab a seat on the patio and check the schedule for live music.

Saturday:

• Grab brunch at Marigold Kitchen downtown (pro tip: their lemon ricotta pancakes = gamechanger).
• Rent a kayak at Brittingham Boats and paddle Monona Bay.
• Spend the afternoon brewery-hopping at Young Blood Beer Co. and Working Draft Beer Company.

Sunday:

• Walk the trails at Pheasant Branch Conservancy in Middleton - it’s gorgeous, peaceful, and way less touristy.
• Wrap with a laid-back lunch at Longtable Beer Café.

2. Vintage Finds + Supper Club Energy Weekend

Friday:

• Hit up the vintage treasure trove at Booth 121 on Monona Drive.
• Dinner at The Harvey House, a modern twist on a classic Wisconsin supper club. You’ll want to make a reservation.

Saturday:

• Morning bike ride on the Military Ridge State Trail, starting in Verona (rent from Atkins Bicycle Shop).
• Late lunch at Sugar River Pizza Company.
• Head to Driftless Chocolates for a ridiculously good truffle tasting.
• Evening at The Boathouse at The Edgewater. Dine with stunning lake views and savor Wisconsin favorites in a vibrant setting.

Sunday:

• Brunch at Sardine. Again, make reservations, it’s a popular spot.
• Spend the afternoon wandering Allen Centennial Garden, a hidden oasis on UW’s campus.

3. Outdoor Adventures + Food Truck Feels Weekend

Friday:

• Happy hour at Lucille.
• Grab dinner from one of Madison’s amazing food trucks. Here’s a live map to find one close to you!

Saturday:

• Morning hike through the Arboretum - peaceful, wildflowers, and not super crowded.
• Lunch at Everly. Grab a seat outside if the weather is favorable.
• Take in the eclectic shops on Monroe Street.
• Evening fun at Garver Feed Mill — they have tons of pop-up music and night markets in summer.

Sunday:

• Grab a giant cinnamon roll at Lazy Jane’s Café.
• Cruise over to CamRock County Park in Cambridge for mountain biking trails or just a nature walk.

4. Quirky Museums + Small-Town Road Trip Weekend

Friday:

• Start with drinks at Eno Vino atop the AC Hotel Madison Downtown – the views are ah.may.zing.
• Then stroll the quirky Wisconsin Veterans Museum downtown - it’s way cooler than it sounds.

Saturday:

• Day trip to Mt. Horeb, aka “MoHo” aka "The Troll Capital of the World."
• Stop by The Grumpy Troll Brew Pub for a craft beer and giant pretzel.
• Visit Duluth Trading Co. HQ and troll-spot along Main Street.
• Dinner at Sjölinds Chocolate House (yes, chocolate for dinner is fine).

Sunday:

• Sleep in.
• End your weekend strolling through the Olbrich Botanical Gardens — free and blooming with color all summer.

Final Tips:

• Bring a bike — Madison’s super bike-friendly.
• Pack a hammock — tons of lakeside parks for a quick lounge.
• Hit up the Dane County Farmers' Market on Saturdays if you’re downtown - it’s the largest producer-only farmers' market in the country.

Madison’s got small-town vibes with just the right splash of big-city energy. However you like to weekend, you’ll find a little something extra here.