Welcome to Sleepy Hollow Bar
Sleepy Hollow Bar, located at 5701 W Jackson St in Pensacola, FL, offers a lively and welcoming atmosphere perfect for locals and travelers alike. Renowned for its engaging karaoke nights and skilled bartenders, this cash-only bar captivates patrons with its charming décor and a cozy outdoor patio. The friendly vibe fosters connection, making it an ideal place to relax while enjoying cold beers or cocktails. With pool tables and a diverse music selection, Sleepy Hollow serves as a community hub where everyone feels at home, delivering delightful experiences that keep guests returning for more.
-
5701 W Jackson St, Pensacola, FL 32506, United States Hotline: +1 850-455-9288
Welcome to Sleepy Hollow Bar, a hidden gem nestled in the heart of Pensacola, Florida. Located at 5701 W Jackson St, this charming bar welcomes all who seek a great time, whether you're a local or just passing through. With an inviting atmosphere, it stands out as an exceptional destination for both relaxation and entertainment.
What makes Sleepy Hollow Bar truly special? Customers rave about the friendly, diverse, and welcoming vibe that envelops the place. As expressed by Oleander, the owners, particularly Jennifer, contribute to a magical experience that connects people from all walks of life. It's this sense of community that transforms a simple night out into a memorable adventure.
The bar features an impressive range of offerings. Whether you're craving a cold beer, a handcrafted cocktail, or an invigorating karaoke session, Sleepy Hollow delivers. From Paula Turner's first Halloween visit to the enthusiastic reviews from regulars like Tom Lazio and Val D., the consistent praise revolves around the quality of service and the lively social environment.
For those who enjoy games, there are pool tables and darts to keep the night lively. The outdoor patio area, praised for its privacy and comfort, adds an extra touch for those who prefer al fresco enjoyment. Mark Dowd describes Sleepy Hollow as “magical,” highlighting its charming features, including a cash-only policy and a space where smoking is allowed, catering to those who appreciate a bit of nostalgia alongside modern fun.
Karaoke nights truly elevate the experience. As many patrons note, it's not just about singing; it’s about getting lost in the moment, sharing smiles, and forming bonds with fellow guests. Whether you’re an experienced performer or a first-timer, the encouraging atmosphere makes it easy to step into the spotlight.
Even if you're simply looking to unwind after a long day, the low-key yet vibrant environment makes Sleepy Hollow Bar the perfect retreat. With affordable prices and a selection of good music at a perfect volume, it becomes more than just a bar; it’s a cozy spot to forget the day and enjoy quality time with friends.
So next time you find yourself in Pensacola, be sure to stop by Sleepy Hollow Bar. Give yourself the opportunity to immerse in the warm camaraderie of a place where everyone feels at home.
Great little bar. Fun tome.
This is an amazing "townie" bar. Our friend "sometimes Karen" brought us there... just some country New Yorkers travelling through. We had a blast. Karaoke was fun. Owners were there too. Would definetly come back and wish this was in my own town! Prices great and service good. Fun people.
Great spot for a cold beer or cocktail and some pool. We stop here all the time , karaoke is fun .
First time going was Halloween night late hrs with my husband. It was decorative on the inside and the bartender (Candy, I think?) was friendly and knowledgeable. It was very clean inside and outside. There was good music playing at the perfect level. It was an overall great vibe. They have an outdoor patio area that gave the perfect amount of privacy and comfort. We will definitely be going back.
I love the sleepy hollow. The owner Jennifer is so sweet. The atmosphere is friendly, diverse and welcoming. There is a variety of music and amazing bartenders. Really just a great place to relax and hang out while you forget about the day you had at work. ...
This bar is magical. They are a cash only bar. Smoking is allowed inside. They have pool tables, seats, an awesome outdoor area, and darts. The charm of this place is all in the Karaoke. I have an absolute blast every time I come here!
My son Marcus and I went to the Sleepy Hollow last night and had a great time! I hadn't been there in many years cause I moved to Georgia but I was in town for Christmas and in the mood for Karaoke! I remember Harry from Sam's and Mr B's and he ain't changed a bit, still just a nice, friendly guy, also his now wife Jamie! Ran into a few old buddies and had a blast and I'll be back before I have to go home!!! Added on June 1, 2023. I was in town again from Georgia and had to stop in for a cocktail and karaoke! Sorry to say I haven't been here in a couple of years and didn't even know Harry passed away RIP Harry...Kim
I play pool here on Monday night and as a relatively new player, they have been welcoming and even remember my name! Tammy, the bartender, rocks!