Discover Downtown Oshkosh

Discover Downtown Oshkosh

Looking to discover Downtown Oshkosh? See what our Downtown has to offer!


Romantic Rendevous
Look no further than your local downtown for a wide variety of intimate & cozy offerings.
By:  Samantha Teal

An afternoon show at The Grand Oshkosh is the perfect setup for an evening of adventure and romance. With its gorgeous interior decor and historic artwork, this downtown favorite is the perfect place to get cozy. The shows varies from local theatre put on by students, to traveling world-class magicians, and much more. No matter what you are interested in, the Grand Opera House has a show for you. So stop on down, enjoy a show, and observe the interior architectural workings. They’ll amaze you.

After your show, make sure to stroll down to Oak’s Candy to satisfy your sweet tooth. They offer a variety of gourmet-style candies and chocolates made by hand right at the store. Oak’s Candy has been around for over five generations, serving chocolate lovers from all over the area with their exceptional quality, value, and personal service. I personally love the milk chocolates. Trust me, if you haven't tried Oak's before, you haven't tried chocolate.

Roxy Supper Club

Be careful not to spoil your appetite for dinner. The Roxy Supper Club on North Main Street is the perfect place to grab a seat with your significant
 other. This fine dining establishment offers luxurious and delicious meals which not only fill you up, but satisfy your taste buds. It’s truly a hidden gem for couples looking to get away for the night.

If you’re lucky enough to be spending time with your special someone during the first Saturday of the month, you can’t miss the chance to enjoy the local downtown Gallery Walk. Downtown Oshkosh lights up during this festive activity from 6:00pm-9:00pm. You can enjoy a romantic stroll along our newly renovated Main Street, which features intricate building architectural for all to enjoy. Special gallerias are set up around the downtown area for all to enjoy free of charge. Sometimes the gallerias are themed, sometimes they display offerings from local students, and sometimes they feature traveling displays from well-known artists, all for your enjoyment. Be sure to check out the interactive map on the Gallery Walk website for a list of participating businesses and for more information.

After all that excitement, you might want to head back to the beautiful and cozy Brayton Bed & Breakfast, a short walk from Main Street. This intimate bed & breakfast offers individual decorated suites at reasonable prices. As you enter through the front door, notice the bright and airy four season’s room that begs you to sit and enjoy that early morning cup of coffee. Step into the foyer with the curved open staircase and you’re greeted with casual elegance and the deep, rich hues that are present throughout the home. The Brayton Bed &Breakfast boasts original architecture inside and out for that feeling of authenticity that you won’t find in any branded hotel.



Downtown Oshkosh Nightlife
Enjoy late evenings with drinks, dinner, music, and more!
By: Samantha Teal

There’s plenty to do in Downtown Oshkosh after hours. Whether you’re looking for happy hours, a place to have dinner, or live music, Downtown Oshkosh offers a variety of venues and historic bars. No matter what you like, you can find it here.

The Algoma ClubAlgoma Club
The Algoma Club is an elegant, detail oriented, hidden space on the second floor of 103 Algoma Boulevard. You’ll love the stained glass windows, hardwood floors, and gasolier-era chandelier. The Algoma Club hosts public and private events, and can accommodate any group. This classy establishment is a favorite for many locals. Come down on Thursday nights and enjoy happy hour! 

Gardina’s Wine Bar and Café
Gardina’s Wine Bar & Cafe is one of the newest additions to Main Street. Within Gardina’s Wine Bar & Café is McKnight & Carlson Wines, previously located on Main Street’s south side. This is the place to try various wines, new specialized recipes, and rich, quality food. Gardina’s is one of the few places in Oshkosh where you can sample various wines along paired with a variety of cheeses. The wait staff is helpful and knowledgeable on all the menu offerings. If you don’t feel like going out for dinner, stop there on your way home and pick out some excellent wine and cheese. If you are really lucky, the owners might have some free samples out during the Farmer’s Market.

Becket’s Restaurant
Becket’s Restaurant is a gorgeous fine dining restaurant settled right on the Fox River. Becket’s can accommodate everything from a nice quiet dinner to your wedding event. They have enough room to accommodate nearly any size event. Located in the City Center, Becket’s has beautifulBecket's patio special event areas to host your perfect evening. Becket’s Restaurant offers one-of-a-kind entrées for lunch and dinner all week long. Weather permitting, they offer an outdoor patio overlooking the Fox River. Becket’s also hosts live music throughout the week. For a complete listing of their upcoming music visit:

Leach Amphitheater
Located right on the beautiful Fox River, the Leach Amphitheater is home to numerous events during the summer. Waterfest, a local favorite, features an outstanding line-up of musical artists ranging from jazz to pop, rock to R&B, and blues to roots music. Concessions are offered on site by local vendors. Waterfest takes place every Thursday night during the summer months. Price of admission is reasonable, and you are guaranteed to have a good time. For specific lineup and ticket prices, please visit Waterfest’s homepage.

Oblio’s Lounge
One of the most beautiful bars in Oshkosh, Oblio’s Lounge is another local favorite. Oblio’s was originally a Schlitz brew house, established in the late 1800’s. The bar features over 25 tap domestic, micro, and import beers. In addition to a great beer selection, the atmosphere is exceptional. With high tin ceilings, hardwood floors, detailed bars, stained glass, and a back outdoor patio, this bar has become one the preferred places to spend an evening with friends. Oblio’s offers shuffleboard, a pool table, darts, and plenty of seating.
Oblio's Lounge



Studying, Socializing, and Indulging in Downtown Oshkosh
Downtown locals take their coffee, and their cafes seriously. Here are some of my favorites.
By:  Samantha Teal

Planet Perk is known by locals as the perfect place to set up a temporary office at a cozy table. With friendly staff, magazines, unique food and drink offerings, and some of the best coffee around, this place is definitely a must-visit in Downtown Oshkosh. There are many “regulars” that get to know the staff, because the majority of them worked there while studying at UW-Oshkosh, located just blocks away. The food and drinks are phenomenal, and many would agree these selections taste like they came right out of grandma’s kitchen.New Moon Cafe

New Moon Café is a centrally located, hip coffee shop right in the center of downtown. The inside is decorated with artwork from local artists and plenty of comfortable seating spaces. New Moon Café offers plenty of choices like hot chocolate, coffee, tea, as well as locally brewed beer. New Moon Café also offers a variety of different soups, sandwiches, wraps, moon dogs, burritos, and quesadillas, among others. My personal favorite in the spicy vegetarian chili, offered daily. The New Moon Café is usually filled with local college students and the like spending time studying, socializing, or listening to late night local music.

Another wonderful place to indulge in some seriously delightful coffee and tea is Caramel Crisp Café. Caramel Crisp is a smaller café filled with a lot more than just hot beverages. It also includes freshly made salads, pasta salads, sandwiches, homemade soups, popcorn, cookies, ice cream, numerous candy offerings, and more! The food is nothing less than phenomenal! Caramel Crisp has a relaxing atmosphere with plenty of seating and natural light. Although lunchtime can become pretty busy, it’s worth the wait. And why not check out Caramel Crisp Gifts & Décor, also connected through the Café. This gift shop has a wide variety of unique gifts such as teas, teapots, coffee mugs, wedding gifts, baby décor, and much more! You can find the perfect unique gift for any occasion.