The Rooftop Lounge Oswego

05/30/2026

Need a little something to believe in this Saturday? Racing is back this evening at Oswego Speedway with the Barlow's Concessions 75th Anniversary Season Kickoff!

Why not stop by The Rooftop beforehand for a cocktail and bite to celebrate! Might we recommend our 'Talk Dirty To Me' filthy 🍸 martini? It features Vodka, Dry Vermouth, Chili -infused Olive Juice, Red Miso Paste, Black Pepper, Infused Spicy Herb Olive Oil, Garnished with Pimento Olives, and Sweety Drop Peppers.

Whatever your particular poison, and no matter the cooler temperatures, join us today as we rev up for summer! 😃

05/29/2026

Live music returns to The Rooftop tonight with local legend 🎶 Larry Kyle from 6–9 PM!

A veteran of the local music scene, Larry has been performing for nearly six decades, has released five original albums with his brothers-based blues group, DAMDOG, and brings that same authentic energy to every solo performance.

With guitar, harmonica, vocals, foot percussion, and more, Larry delivers the kind of one-man show that keeps audiences entertained all night long. Come enjoy great music, great food, cold drinks, and an unforgettable evening at The Rooftop. 😃

05/28/2026

When you think of signature dishes at The Rooftop, one contender rises right to the top: our Ahi Tuna 🍣.

Featuring 4 ounces of premium sesame-crusted Ahi Tuna, expertly seared and served over a bold Wasabi Crème, this dish is finished with Soy Sauce Pearls, Pickled Ginger, and a rich, velvety Teriyaki Glaze. Bright, fresh, and packed with flavor, it’s the perfect summer plate, as unforgettable as an Oswego sunset.

Think you know which dishes made our Top 5?

Stay tuned. 😉

05/27/2026

It is going to be a gorgeous, early summer day here in The Port City, and if that's not enough to get you excited, we have another reason: The return of Music Bingo!

From 7-9 this evening, you can test your music knowledge and enjoy a little friendly competition amongst friends, not just for bragging rights, but for some nice prizes as well!

The 🌞 sun is out, the vibe is tight, and we hope to see you for good food, fun, and more! 😃

05/26/2026

Memorial Day Weekend may have come and gone… but your post-BBQ waistline still has room for one more treat. 😉

Our Belgian Vegan Gluten Free Caramel & Chocolate Dessert is the perfect way to finish the long weekend on a sweet note.

Featuring a rich Chocolate & Caramel Square made with agave, coconut oil, hazelnuts, and buckwheat on a date and almond crust, all topped with chocolate drizzle and fresh fruit. Decadent, gluten-free, vegan… and absolutely worth it. 🍫✨

05/25/2026

05/22/2026

Friday night + rooftop views + live 🎶 music from Ron Hurne = a pretty solid way to kick off Memorial Day weekend.

Won't you join us? 😊

05/21/2026

Summer drink specials are arriving at The Rooftop just in time for Memorial Day Weekend ☀️🍸

First up: our Pink Lemon Drop Martini, featuring Deep Eddy Lemon Vodka, dragon fruit syrup, edible glitter, and house-made dehydrated pink lemons. Bright, refreshing, and just the right amount of fun!

Mother Nature may be giving us more rain than rays this weekend, but this cocktail is here to bring the summer vibes anyway. Stop in, sip something bright, and kick off the unofficial start of summer with us at The Rooftop. 😊

05/20/2026

Next up amongst our newest menu additions: Peach & Ricotta Flatbread!

Made with Ricotta, Grilled Peaches, Mozzarella, Burrata, Bell Peppers, Red Pepper Flakes, and a drizzle of Hot Honey, this savory-meets-sweet creation delivers the perfect balance of creamy, fresh, smoky, and just a little bit spicy. 🍑🔥

Even better? It’s vegetarian and can also be modified to be gluten-free, making it a great option for just about everyone at the table.

Summer is knocking on the door, and we're ready to embrace it with arms wide open here at The Rootop! 😃