The Rooftop Lounge Oswego

10/14/2026

It is a comfort food kinda week here at The Rooftop, and we have two great specials that fit the bill: a Garlic Parmesan Asiago Gnocchi as well as a Cheeseburger Flatbread.

Hungry?

Stop by, warm up, and enjoy some restorative dishes that feed the soul as much as the body 😃.

10/13/2026

🍸 Your Tuesday just got a little happier! 🙂

Why wait for the weekend? Join us at The Rooftop today from 4–6 PM for Happy Hour and enjoy some great deals on your favorite drinks and bites!

🍷 20% OFF W**e by the Bottle

🍺 $2 OFF B**r & Menu'd Cocktails

🍽️ $2 OFF Small Plates

Whether you're winding down after work or catching up with friends, we've got just the place (and specials) for you!

See you at The Rooftop! 🥂

10/11/2026

Another wonderful evening at The Rooftop Lounge!

A heartfelt thank you to everyone who joined us for our sixth Bourbon & Cigar Pairing Dinner! We're grateful to our incredible patrons, our dedicated staff, and our event partners for helping make the evening another great success.

Great food, exceptional bourbon, fine ci**rs, and even better company. We couldn't ask for more!

Cheers to everyone who made it possible. We look forward to seeing you at the next one! 🥃

10/10/2026

10/09/2026

It's no myth! 🥃🚬

We're down to just TWO TABLES for our sixth Bourbon & Cigar Pairing Dinner, happening tomorrow evening, Saturday, October 10th, at The Rooftop!

Still on the fence? Here's a little something to tempt you...

Our friends at Mythology Distillery who are partnering (along with Rockys Ci**rs) with us for the evening, have generously shared their Small Batch Syrah Finished Wh***ey with our kitchen team. The result? A delicious Rosemary & Blackberry Reduction, specially crafted to complement the third course of the evening.

And what, exactly, is that third course?🙂

Well, we're not giving away all our secrets! Give us a call, and we'll see if we can tempt you into claiming one of those last two tables.

Don't miss out! Tickets are still available at www.therooftoplounge.com.

10/09/2026

The long weekend is here, and we're kicking it off this evening with some great live 🎵 music courtesy of Rooftop regulars PK Experience.

Good food, good drinks, and more. All that is missing is you 🙂

10/08/2026

Looking for a trio of amazing cocktails? 😃

Our Fall Margarita Flight includes: Apple Chai, Banana Ginger, and Cherry Rosemary.

Are you thirsty this Thursday? Stop by The Rooftop, enjoy the fall sunshine from our terrace, and get a head-start on the long weekend!

10/07/2026

Still on the fence about attending the Rooftop's 5-Course Bourbon & Cigar Pairing Dinner on October 10th?

Only a few tickets remain! 😲

Go to the following for more information and to make a purchase:

https://www.eventbrite.com/e/whiskey-cigar-pairing-dinner-at-the-rooftop-lounge-tickets-2000172326271

10/06/2026

A quick start-of-the-week update from The Rooftop! 🙂

First and most importantly, we’re making some 🤖 technology upgrades this week as we transition to Toast, our new point-of-sale system. As with any new system, there may be a bit of a learning curve, so we appreciate your patience with our staff as everyone gets comfortable with the change!

We also have a couple of adjustments to our lunch 🕑 hours this week:

Tuesday & Wednesday: We will be closed for in-person dining from 11am–4pm. However, online ordering will be available beginning at 1pm both days.

After 4pm, we’ll be back to our regular schedule and ready to welcome you upstairs! 😃

Thanks for bearing with us during a slightly unusual week. We appreciate your patience, your understanding, and, as always, your support of The Rooftop. See you soon! 🍸