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A Memorable Weekend in Madison: Your Complete LGBTQ+ Itinerary

Madison, aka Mad City, Madtown, or the People’s Republic of Madison, is a super queer and lesbian-friendly spot in Wisconsin. Known as a university town, it’s packed with young people. The city is growing rapidly and continues to emerge as a great place for young, progressive professionals to call home. 

It’s a city where LGBTQ+ businesses are thriving in multiple industries. With help from our friends at Destination Madison, building a weekend itinerary that features tons of LGBTQ-owned businesses was a piece of cake. 

Madison celebrates Pride in August, but this is a city celebrating the city year-round. Use this article to plan to your Pride weekend or any weekend in Madison.

Day 1 (Friday)

Check in to the Moxy Madison Downtown

Spend your weekend at the Moxy Madison Downtown. We also loved the location—just a few minutes from the square and a quick bike ride to the Willy neighborhood.

The rooms are spacious. The double room has a cool layout with the bathroom between the beds, so it feels like two separate rooms. Each bed has its storage and TV, which is great for groups.

Downstairs, there’s a super stylish and inviting bar. The lobby and second floor have big couches and TVs, perfect for hanging out with friends and family. 

At check-in, we got a fun drink chip to use at the bar. Since we don’t drink alcohol, we loved that it could also be used for a latte or a mocktail.

Eat Lunch at Lucille

Lucille, located downtown, offers a great mix of locally sourced and globally-inspired dishes. Their menu features wood-fired pizza, Wisco-Detroit cheddar-crusted black steel pan pizza, and delicious Pan-Latin cuisine. 

The bar, specializing in rum and tequila, is housed in a former bank with a swanky speakeasy-style events venue in the old basement safe.

I loved the Wisco twist on Detroit-style pizza and the delicious, generous guac portions. Seeing rainbow flags and pride event fliers made me feel right at home as a queer person, especially at our first meal in a new city.

Grab a fun Drink

Sencha Tea Bar

We stumbled upon Sencha Tea Bar an easygoing counter-serve spot offering iced, bubble, and hot tea, plus coolers and shakes. The Trans Youth sign by the door caught our eye, and we knew we had to check it out. The menu is packed with fun and innovative flavor combinations I’ve never seen before. We grabbed a Thai tea to share and having recently spent three weeks in Thailand, I can say it was just as good as the ones we had there.

Fair Trade Coffee House

Located on State Street, just a few minutes from the Capitol, Fair Trade Coffee House is the perfect spot to stop while exploring downtown. I grabbed an oat milk latte, and Meg tried one of their Italian sodas. They use fair trade beans to craft amazing coffee and espresso drinks. They also serve breakfast and lunch and house-baked goods daily. Plus, it’s one of nine LGBTQ-owned coffee shops in Madison!

Visit Madison Museum of Contemporary Art

The Madison Museum of Contemporary Art is an awesome spot showcasing modern and contemporary art that educates, reflects, and inspires. It’s an independent organization with a stunning rooftop overlooking State Street. We were lucky enough to catch a fantastic exhibition by William Villalongo called Myths and Migrations. Villalongo, a Brooklyn-based artist, creates striking visual narratives that explore the complexities of Black existence.

Installation view of William Villalongo: Myths and Migrations, Madison Museum of Contemporary Art, 2024. Photo Courtesy of MMoCA

The museum itself is a beautiful space to walk through, and we loved that it has free admission.

Happy Hour at Delta Beer Lab

Delta Beer Lab is all about building community through quality, local craft beer and welcoming everyone. The taproom has shuffleboard, darts, and board games, and you’re encouraged to bring your own food. Of course, they have killer beers including a fun seasonal rotation. 

When we visited, there was an awesome Pride event happening. There was a food truck, live music, and several tables with info on how to get involved in Madison’s LGBTQ community, like queer book clubs through A Room of One’s Own Bookstore, and info on the gay hockey league and roller derby team. They also make house sodas, which is great for someone who doesn’t drink much but still wants to join in and support.

Dinner at The Old Fashioned

Get the full Madison experience with dinner at The Old Fashioned, an LGBTQ+-owned spot by Chef Tami Lax. This place is it for classic Wisconsin cuisine and home to the best cheese curds in the country, according to some. Trying cheese curds was at the top of my Madison bucket list, so it was a must visit. The Old Fashioned has an old-school feel and was buzzing with great energy during our visit.

We wanted to try a few other Wisconsin classics too. I ordered a Shrub, a drink mixing fruit and vinegar, along with the Wisconsin Classic Fish Fry. Meg had the Pork Schnitzel with Door County cherry mustard sauce, German potato salad, and braised caraway cabbage. The portions were massive and everything was delicious. It’s a can’t-miss meal to kick off a weekend in Madison!

Day 2 (Saturday)

Day two is all about shopping local, from browsing the farmers market to checking out thrift shops and specialty boutiques. Before heading to a sporting event, take advantage of all the incredible options to celebrate women in sports.

Cargo Coffee

Grab a cup of coffee at Cargo Coffee, located across the street from the hotel. It’s a short walk up to the farmers market, and because it’s a producers-only market, you won’t find any coffee available in the main part of the market around the Capitol. Cargo Coffee is a great place to kick off the day. The coffee was strong, and we enjoyed the Pride menu filled with seasonal specials. We opted for iced lavender lattes and took them with us for the short walk to the market. And, surprise, this is another one of the LGBTQ- owned coffee shops.

Dane County Farmers Market

The Dane County Farmers’ Market takes place on the square, making a full lap around the Capitol building every Saturday morning. Over 100 vendors sell like produce, flower and baked goods. It is the largest producer-only farmers’ market in the country which means you are buying directly from the people who grew or made the item being sold.

Arriving early is key if you’re buying lots of produce or looking to avoid crowds. You’ll see local chefs looking for the freshest ingredients a little before 7am.  

We strolled a full lap around the Capitol. It was bustling, but the flow on the sidewalks made it manageable. Staying at a hotel meant we couldn’t take home any produce, but we were tempted by the beautiful flowers for our New York home. We picked up cinnamon bun sticks, a potato donut, and a pint of gorgeous strawberries, then settled on the Capitol lawn for a delightful picnic of delicious bites and great people-watching.

Farmers’ markets hold a special place in my heart, and this one exceeded expectations. I can see why locals rave about it and encourage visitors to experience it firsthand.

Search for Thrift Finds

Singlestich Madison

Singlestitch, has a unique collection of vintage pieces and memorabilia. It’s a well-curated selection, with plenty of Packers and University of Wisconsin gear towards the back.


Ragstock has a bunch of new and used stuff. I loved their collection of vintage collegiate sweatshirts. It would have been easy to leave with 5-6 new pieces. 

Do Some Shopping


August is a cool streetwear and shoe store. Their selection has elevated pieces and it’s done in a very aestetic way. The store had a very gender neutral feel but probably leaned a bit more masc of center. If you’re looking to elevate a masc wardrobe I’d encourage you to stop by or flip through the website. 


Fromagination, an LGBTQ-owned cheese shop on Capitol Square opened in 2007, they feature award-winning Wisconsin artisan cheese. They also offer cheese pairings, beer, wine, meats, chocolates, and more.

We stopped by on a Monday afternoon and noticed a constant flow of people grabbing their sandwiches—they must be amazing! They also have gift sets, I was tempted to send one to myself. 

Square Wine Co. 

Check out Square Wine Co. an LGBTQ and woman-owned wine shop in Madison, all about wines from small, family growers that capture their roots. They’re hands-on, with weekly tastings to help you find wines that truly speak to you. Wine’s a living thing, always evolving in the bottle, and they’re excited to share this magical journey with you. We had a blast sipping a few glasses in their cozy front room and checking out their awesome wine selection, wishing we could bring some home with us.

Grab a Late Brunch

Monty’s Blue Plate Diner

Monty’s Blue Plate Diner on Atwood Avenue is a beloved spot with classic diner favorites—think milkshakes, pie, biscuits and gravy, scrambles, and pancakes.

Housed in a retrofitted old gas station, Monty’s brings a cool 50s-diner-meets-hipster vibe. We both tried their burgers, which were delicious and exactly what you’d expect from a diner. What surprised us was their extensive separate menu featuring vegan twists on diner classics like almond milk French toast.

Pro tip: You can still enjoy their classic diner milkshake dairy-free!

Go to a Sporting Event

Madison has an incredible women’s sports scene, in many way rivaling much bigger US cities with unwavering community support. Womens athletics has had a recent boot in popularity but whats really cool is that Madison has been celebrating women and the LGBTQ community in sports long before this year. Madison Forward reps were seen at various Pride events, and our Queer + Lesbian Travel Facebook group highly recommends catching a match with the Mingo Ladies, an inclusive space for all women. The community, known as The Flock, passionately backs LGBTQ+ pride and social movements.

In addition to its thriving LGBTQ+ community, Madison boasts numerous outstanding women’s sports teams. From the perennial powerhouse Wisconsin Women’s Volleyball team to women managing the Madison Mallards, a collegiate summer baseball team, and the Madison Blaze women’s football team, there’s a diverse range of athletic opportunities. Notably, the Madison Gay Hockey Association hosts free games every Sunday evening from October to March, while the Madison Minotaurs represent in the gay rugby league. Looking ahead, Madison anticipates the arrival of pro soccer and volleyball teams, alongside the launch of a groundbreaking collegiate softball league showcasing top female players nationwide. Catch a game, any game, it’s a sports town.

Eat  Dinner at D’Vino 

If you haven’t already indulged in stadium eats (totally understandable!), make your way to D’Vino, a charming Italian restaurant offering both indoor and outdoor seating. It’s perfect for a little date night. The service was warm and welcoming, and the food was absolutely delicious. We opted to share several dishes, and the burrata crostinis, chicken parmesan, and ricotta zeppoli were our favorites for us.

Pop Next Door for a Drink at WOOF’S

WOOF’S is one of Madison is lively gay bars with a sports lean. It’s lively and they have good drinks and some games like darts to play. It leans towards a gay male audience but it’s welcoming and a great option to pop in for a drink before heading back to the hotel.

Day Three (Sunday)

Madison is one of the most bikeable cities in the country, with miles of bike trails and paths weaving through the city. This full day can, of course, be done with a car or an Uber, but we enjoyed spending time outside soaking up some sunshine, making plenty of stops along the way, all rides shorter than 15 minutes. You’ll also close out your Madison weekend itinerary with a visit to a classic Wisconsin supper club.

Grab some BCycle Bikes 

Take on the day with Madison BCycle. Download an app and you have 39 convenient places to pick up and drop off bikes from. The bikes are ebike making it even easier to cover large chunks of the city. We had a great time zipping around and were both pleasantly surprised by how much boost comes from the bikes when riding uphill. Neither of rides often so having the bike lanes and paths made it feel fun and not at all stressful. 

To download the app, click here for the BCycle App, and to locate the stations, check here.

Have Breakfast a Willalby’s Cafe

There is something uniquely delightful about a classic diner on a Sunday morning and Willalby’s Cafe is a wonderful version, plus it’s LGBTQ+ owned. Their pancakes are gigantic—thin and crispy, unlike your typical flapjacks, but delicious. I almost ordered two, but our waiter wisely warned us about their size—they’re larger than a dinner plate! The coffee was bold and plentiful, thanks to the excellent service. We also enjoyed discovering their solid selection of vegan options, which was a nice bonus.

Peruse the Shelves at A Room of One’s Own Bookstore

Just a quick 9-minute bike ride from Wallaby’s, A Room of One’s Own is your go-to local, independent feminist bookstore. They’ve got an extensive LGBTQ fiction and nonfiction section, specializing in feminism, and gender studies, including highlighting transgender authors with their own dedicated space. With around 200,000 titles, the bookstore features staff picks marked with handwritten notes that with thoughtful insights on their selections. It’s one of the most thoughtful and progressive collections we’ve come across. I especially enjoyed browsing their children’s books and imagining how impactful they would have been for young Lindsay. Plus, they host cool events like Queer and Trans open mic nights, and book clubs such as the Gender Fluid Book Club and Queer Joy Book Club. It’s more than just a bookstore—it’s a community hub.

Visit Olbrich Botanical Gardens

Olbrich Botanical Gardens is a laid-back spot, just a 15-minute bike ride from the bookstore, ideal for a stroll or to stretch your legs. Admission is free. You can explore beautiful landscapes like the Thai Pavilion and Garden, a serene Rose Garden, and diverse plant collections. Pop across the street to take a peek at Lake Monona before heading out. 

Michaels Frozen Custard 

Michaels Frozen Custard serves gourmet frozen custard, burgers, and hot dogs in an old-school setting with red and white striped umbrellas providing plenty of shady outdoor seating. Their extensive menu includes sundaes, Twisters, floats, and shakes with fun and unique combinations—just be mindful not to panic order like I did the first time (but it was so good we went twice!). Meg loved the Reece’s Peanut Butter Cup sundae, while I enjoyed the Crazy for Cookie Dough Twister on our first visit. The second time around, I opted for something more unique: a Key Lime Pie Twister.

When you’re done take the leisurely 15-20 min ride back to the hotel and freshen up. 

Experience a Wisconsin Supper Club

Now that you’re all dressed up head to The Harvey House to close out your weekend in Madison. Located behind Madison’s Historic Train Depot. The Harvey House celebrates Wisconsin’s iconic supper clubs. Restored by Midwest natives Shaina and Joe Papach, this former Baggage Claim House now blends 19th-century charm with modern design. You can expect live music playing Big Band or Classic Jazz music. 

We shared a beautiful meal that started with The Harvey House take on the classic relish tray. The meal was impeccable from start to finish, we enjoyed the food, particularly the French Onion Bouillon, Chicken Schnitzel, and Pavlova. We loved the slow pace of the meal. Meg had a glass of bubbles to start the meal and I had a lovely fruit-forward mocktail recommended by the server. We sat at a table near the open kitchen a it really felt like dinner and a show. The organization and precision required to turn out high-quality food like this is mesmerizing to watch. 

We loved our time in Madison. Not only are we hopeful to return one day we are excited to share with other queer women how beautiful and welcoming Madison is.

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