Everyone loves a Wisconsin summer. We might be biased, but summers in Oshkosh are the best! There are tons of fun things to do, see and explore in Downtown Oshkosh, especially during the summer months. Here are our top 10 favorite things to do during the summer in Downtown Oshkosh.
1. Farmers Market
The Oshkosh Farmers Market is held at the 400 & 500 Blocks of N Main Street every Saturday, June-October from 8am-12:30pm. The market has more than 120 vendors with products ranging from produce, flowers, food trucks, and craft vendors. The Oshkosh Farmers Market has been voted as the 2nd best Farmers Market in Wisconsin, closely following the Madison Farmers Market, and is the perfect summer activity in Downtown Oshkosh!
2. Live Music in Downtown Oshkosh
What better way to enjoy the summer weather than live music outside. Downtown Oshkosh is a hot spot for live music during the summer months. Whether it’s live music in Opera House Square or local bands playing at your favorite outdoor side yard or patio, there is music for everyone to love. Music on Main takes place every Wednesday June through August in Opera House Square - with both evening performances and family friendly bands - be sure to check the schedule here for the lineup and times!
Other live music events include: Oshkosh Waterfest, which takes place at the Leach Amphitheater on most Thursday evenings June-August + Oshkosh Jazz Festival, which takes place the last weekend in August, and ample other live music performances throughout the summer at bars and restaurants in Downtown Oshkosh.
3. Patios and Happy Hour
Our Downtown Oshkosh restaurants and bars love to invite the community through their doors and onto their patios for the summer season. Downtown Oshkosh has many options when it comes to Happy Hours outside in the summer sun!
Be sure to check out:
- Fletch’s Local Tap House
- Anchor + Port at the Downtown Marriott
- Gardina’s Kitchen + Bar
- Bar 430
- Becket’s
- Barley & Hops
- Oblio’s Lounge
4. DORA
Downtown Outdoor Refreshment Area (DORA) is a program that allows patrons to purchase beverages from bars and restaurants and walk outside in the designated area with them. This allows you to bring your favorite beverages from downtown bars and restaurants to Music on Main, on your way to Waterfest, or as you stroll throughout Downtown Oshkosh. Learn more about the DORA program!

5. Riverwalk
The Oshkosh Riverwalk runs along the Fox River and offers opportunities for fishing, dining and recreation. The Riverwalk can be accessed from places like Riverside Park, Boatworks Park, Oshkosh Senior Center and UWO Alumni Center, or via waterway. Each section of the Riverwalk offers a little something unique, such as local fishing spots or patio dining at local restaurants. For more info and a map of the Oshkosh Riverwalk, visit here!

6. Public Art
Downtown Oshkosh has many local, talented artists who love to share their creative passions with the community. Over the past couple years, a surplus of public art has enhanced our downtown area with murals on the sides of buildings and businesses to create a bright and beautiful downtown. Some of the town's favorites are the Greetings from Oshkosh mural located at 563 N Main St. and the Algoma Alley art located at 108 Algoma Blvd. Our downtown murals are beautiful locations for pictures and admiration! Learn more about public art in Downtown Oshkosh, visit here!
7. Opera House Square
Opera House Square is the heart of Downtown Oshkosh! A great central location to provide the community with ample fun activities and events. This is where Music on Main, Chalk Walk, Square Faire and many other fun events are held. There is plentiful space in the square to have a picnic, play frisbee or yard games, do yoga, play with your dog, or simply enjoy the ambiance of Downtown Oshkosh.
8. Beat the Heat
Downtown Oshkosh small businesses and cafes offer a variety of places to stop and get a cold treat to beat the summer heat. If you’re looking for an ice-cold, refreshing drink or a frosty treat on your stroll downtown, Planet Perk, Pivot Nutrition, Elsewhere Market, Caramel Crisp, and New Moon Cafe are the perfect places to stop, offering an assortment of icy beverages and cold sweet treats. A few of our favorites include the ice cream flight at Caramel Crisp Cafe, a toffee coffee smoothie from Planet Perk Cafe or the summer seasonal drink flight at Elsewhere Market.
9. Shop and Stroll
After dropping by to get a cold beverage or a frosty treat, wander down our beautiful streets to find one of our many places to shop. Downtown Oshkosh offers a variety of retail destinations for all to enjoy – check out our downtown boutiques featuring summer clothing and accessories as well as fun vintage finds and lots of options for the thrifty shopper. You can also find local groceries, game stores, home decor boutiques and more!
10. Pedal Trolley
A perfect way to get outside, drink and get a workout in, is with the Oshkosh Pedal Trolley! On this pedal tour, you can sightsee, listen to music and of course pedal your heart out throughout Downtown Oshkosh. It is the perfect activity for bachelor or bachelorette parties, work outings or hanging out with a group of your friends.

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