Cypress & Oak

Allow me to share the tale of how Cypress and Oaks became our preferred dining establishments. Upon entering, I instantly sensed that I was in capable hands. The server was exceptional, and the "Mull It Over" hot drink, paired with the sight of snow gently falling outside the window, provided a comforting warmth that enveloped me from within. This venue truly feels like paradise. If you have not yet visited, I highly recommend making a reservation, and if you find yourself in Frankfort, be sure not to overlook this gem! 100/out of 10

Everything I ate was delicious, I was tempted to actually lick my plate.

Incredible food, unbeatable ambiance, wonderful hospitality, and a great choice for date night. My husband and I went for dinner with another couple. The server was kind and knowledgeable. I would recommend the steak with smashed potatoes along with the Old Fashion. 🥃 Well worth the experience!

A great experience! We were a party of 6. Everyone’s food was excellent. Jennifer was our waitress and she was wonderful. We will definitely be back!

We stayed at The Delegate adjacent hotel and what an incredible combination! C& O is a beautiful establishment and you’re amazed as soon as you walk in. Very posh yet comfortable. We sat in the bar for drinks and dessert. Our bartender was very friendly and helpful even though they were getting busier the hour and change we were there. They have a nice cozy vibe that comes easy for them. Relaxing and upscale without having to get dressed up yourself. Will absolutely be back! Well done!

Recently celebrated my Mother's 90th birthday at Cypress and Oak. We had dinner in the private dining room for a party of 17 and it was outstanding. The director of banquets and events, who worked with me to organize the dinner, was highly professional, accessible and very accommodating to all my requests. The venue is charming and the dinner and bar staff did a great job serving the guests and were very friendly and courteous. The drink selection, including the wines were great and the food was excellent!!! I highly recommend the steak medallions and the butter cake was awesome. Well done Cypress and Oak and thank you for your efforts to make my Mother's birthday a very enjoyable celebration!

I thought it was great. The food was delicious. Service was a little slow, but we were a large group. The server was good but she should have had more help. To keep this top notch restaurant up and running to meet the high standard of foods it represents the service should be top notch! If you can get more servers I think it will be a breath of fresh air for Frankfort. We need a classy restaurant like Cypress & Oak.

This restaurant exceeded my expectations beyond measure. My girlfriend and I arrived without a reservation on one of the opening nights… we saw the sign out front and just walked in. We were met with smiling faces and they told us they could seat us anyway. Chastity was our server, she was spectacular! Very professional and extremely polite. The managers came by to check on our table a few times and they were super friendly. They recommended drinks and their recommendations were spot-on! Lastly, special shout-out to Roger for double-checking on dinner and just making sure our date night was special. 10/10 we will 100% be back. The steak medallions will blow you away and my girlfriend will not live without another one of those espresso martinis. GREAT JOB CYPRESS AND OAK TEAM!

Our waitress Amy was so wonderful she was very fast and efficient and very sweet. and we enjoyed her help and the food was so delicious and tasted amazing

I had an absolutely wonderful experience at Cypress and Oak, thanks in no small part to our amazing server, Jesyka. From the moment we arrived, she greeted us with warmth and professionalism, making us feel welcome and at ease. She was attentive without being overbearing, offering great menu recommendations and ensuring that we had everything we needed throughout our meal. Now, let’s talk about the food. Every dish was a masterpiece. The flavors were bold and expertly balanced, with ingredients that were clearly fresh and thoughtfully sourced. Whether it was the appetizers, entrees, or dessert, each bite was a delight. You can tell that the chefs at Cypress and Oak truly care about their craft.

Excellent service and dinner! Drinks were top notch, can’t wait to go back! Food quality was great!

Fabulous steak and cocktails. Jan was an excellent, friendly and conscientious server. Overall highly recommend.

SO happy to have a nice date night/night out spot in Frankfort! We loved the cozy yet modern atmosphere and the open kitchen. Service was great and we were happy with everything we tried on the menu – try the wild mushroom hand pie! We'll definitely be back.

Perfect ambiance. Super well designed. Extreme attention to detail. Food was eaten before photographed. Sorry! Cocktails, of which there were many, were spot on, unique, seasonal, and interesting. Service with Ashley was intentional and she took care of our every need. Obviously well managed as crew was on top of it. We will be back for the seafood tower. The steak was marvelous. Meatballs and pasta was rich and spicy. Filet and potatoes was perfectly coked, juicy, and flavorful. Good quality and solid price point for the experience. 5 stars in all categories!

Stopped by for lunch. Our waitress and kitchen staff were very helpful answering allergy related questions, which is so much appreciated. Lunch was reasonably priced, atmosphere feels very upscale and warm, food was delicious. We will be back! So excited to have this option in Frankfort.

We had a great dinner last night with 10 of our closest friends to celebrate my husbands birthday. Jesyka was our server & she was great! She took awesome care of us all and made sure that we all had everything we needed/wanted. The food and our drinks were all amazing. The filets were perfect and make sure you try the spicy beef handpies! My husband and I had been there twice in the past, both times we were impressed and this time was no exception.

If I could give 6 stars I would. The food and service were exceptional. The food was so good, we tipped the kitchen separately. Amy was our server, she was attentive and spot on with recommendations. The whole thing was awesome. We cant wait to go back. It was worth every cent. I had the Hanger steak and my wife had the “shells and shells”. I got the parm truffle oil fries on the side and they were also incredible. We literally talked about it the whole way home. Im telling you, just go!

We just happened to stay at the Delegate hotel in Frankfort and stopped into Cypress & Oaks . The food was Amazing, Chef Bob was incredible. But Johnny the bar bartender made our night. Make sure you stop in . You won't br disappointed

Great meal and great service. We asked our waitress Jessica for some recommendations and she was spot on from the cocktails to the entree. We will definitely be back the next time we visit Frankfort.

Found this gem when we were suppose to be going to another restaurant for dinner! We were not disappointed with our detour! This positive vibe, romantic casual, feeling of downtown but with all the country charm restaurant exceeded our expectations in every way! Our bartender/server, Jennifer shared with us the menu details, made recommendations and then served us up an amazing old fashioned and wine! After a day of driving we just wanted to melt into a good hearty dinner and Cypress & Oak did just that! Portions were great! We highly recommend the meatballs made with several amazing meats and the pasta was freshly made as well! Chef kiss to this delightful place!

Stopped in for dinner while visiting Frankfort and were blown away. The food is amazing—especially the filet mignon. One of the best steaks I’ve ever had—perfectly cooked, tender, and full of flavor. Great atmosphere and friendly service too. We’ll definitely be back next time we’re in town.

Such a great dinner — ambiance was great, food was outstanding. Becca was a great server, offering recommendations along the way. Would highly recommend for out of town visitors and locals alike.

My husband and I decided to dine at this restaurant on a whim, and we had an absolutely wonderful time. The atmosphere was great, the drinks were perfectly made, and the food was delicious. Our server/bartender, Jen, was amazing. She not only explained the history of the building but also gave us a sneak peek at the new menu coming out. We even got to tour the hotel, which has been beautifully redone. We’ll definitely be making this place a regular spot.

I stumbled across Cypress & Oak on a business trip looking for a decent restaurant for dinner. This place blew me away! The ambience is modern yet classy. My waitress, Jennifer, served several tables while helping at the bar. She was very attentive, timely, and very pleasant. The food was amazing! Everything was so great that I came back the next night. Between both nights, I had the herb roasted Cod, 7 oz Filet w/ truffle herb butter, parmesan truffle tallow fries (!!!!!), and side salad. The filet was the most tender, mouth watering, perfectly cooked steak I've had in years! I hope I get to come back to Frankfort again soon just to eat here again. Thank you Cypress & Oak chefs, waiters, and staff for making this an unexpectedly memorable event for me!

Pretty good. Solid chicken n mushrooms. Possibly a bit generous with the 5 stars but no complaints. Alas: five stars!

The bar staff were very accommodating and friendly. The bartender was making incredibly tasty cocktails. We had a fantastic dinner at the bar and the food was exceptional. Since they had just opened, their dry aged steaks were unavailable. We ordered the bone-in ribeye, it was perfectly cooked, flavorful, and tender. The only sore point was the hostess. Not very welcoming or accommodating, so much so we almost left. Glad we chose to find our own way to the bar and experience this new interesting spot.

Great place, the building gets 5 stars, the furniture and tableware gets 5 stars, the food gets 5 stars, our server needed a little polishing for this caliber of dining. But all is good. We will be back.

We went here for Valentine’s Day and my wife’s Birthday…we were greeted promptly and led to our table, that was a high top/booth hybrid facing the open kitchen! Wife wasn’t too thrilled with that but it worked. The service was adequate but kind of slow honestly…slow to take our order, slow with drinks, slow to serve the food! We were sitting across from the open kitchen so we watched the food get prepped, hit the warming area, and sit there for a while. Our son’s cheeseburger sit there more than 15 mins and our steak meals sit there for almost 10 mins!! Honestly the son said burger was very good just a little cool, my filet was almost perfectly cooked and seasoned very well. The problem was the idea hanger steak…it was rare when she asked for medium well!! She is not one to complain , so she didn’t say anything until we got home and showed me the steak. For Valentine’s night they were busy but not busy like a lot of places, food was mostly good once served and service was okay. For the money it should have been much better!

Loved the ambiance and the drinks, but the service was seriously lacking. The bartender was unfriendly and our server was kind but disappeared a lot. We ordered the $87 steak and were never asked how it was- which wasn't good. It was over cooked and grisly but had to eat it because our server was no where to be found and we were starving after having to wait so long to order.

This is a distinctive looking restaurant in a unique historical building in Downtown Frankfort. We started with seasonal cocktails which were very enjoyable and an appetizer of Kentucky Fritters which were good. We shared an excellent bowl of roasted red pepper soup (which was a creamy and rich bisque). The meat balls served on linguine were quite good, especially the sauce. The meatballs needed some spice but were tender and moist. The disappointment was the burger. It was served several minutes after leaving the grill. The bun may not have been toasted and it was a rapidly cooling soggy mess after a couple of bites. Unremarkable flavor, a greenhouse tomato in late July when local tomatoes are plentiful, and simply did not resemble the menu description. The fries were warmish and acceptable. The service was average but acceptable. We will try this restaurant again but will stay away from the burger (which I thought was a safe choice!) next time.

I was excited to try this new restaurant, and the atmosphere did not disappoint—modern, stylish, and beautifully designed. However, the food was a major letdown. While not terrible, it felt completely out of place for such a well-crafted setting. The quality was more on par with fast food, yet the prices suggested a near fine-dining experience. Unfortunately, it just didn’t match up. I won’t be returning unless they revamp the menu to align with the overall vibe.

The atmosphere was great, the service was good as well. Why two stars, you ask? 'Cause you can't call yourself a steakhouse if your meat is stringy and devoid of flavor. I would love for this local restaurant to thrive. Please hire somebody with taste buds before you fly out another $90 steak. Frankfort deserves better.

We were passing through and decided to have a nice dinner. Made a reservation for two at the bar because that was what was available. Got one round of drinks after waiting 15 minutes. Sat for another 30 without being offered food menus or another round. Asked to be moved to a table. Once we were moved we sat another 15 minutes without another drink. Never once in the 1hr we were there, did we receive food menus. Super disappointing. Giving two stars because the one round of drinks we did get were good.

Last night 10/20 my wife and I had a dinner reservation for our anniversary while staying in Frankfort. The restaurant was clean and looked like a nice place but the food was quite the let down. We both had filets cooked med rare which were both over cooked and had absolutely no seasoning whatsoever. The cut of meat was quality and was very tender but was just meat. My side was a Cesar salad which I've had better at a subway and my wife's truffle fries were cold and wasn't all that great. Our waitress is believe was Jenn came and took our order brought our drinks and wasn't seen again until after we were done eating, she was nice but was busy behind the bar. So for two old fashions two filets a salad and french fries was $130 plus a $25 tip we should have went to Goodwood brewery because their food was much better.

I really wanted to love this place. Me and my husband are such foodie’s. The steaks were So underwhelming, flavor-wise. I even had to send mine back bc it was room temperature… :( we waited forever for our food..and there’s no bread on the table while you wait. Really unfortunate

Very attractive place. Our server was very good. Our app and wine choices were unavailable. I had ordered a Caesar salad and a sauce to go with my ribeye. Had to remind the woman who brought the food I had it. My friend never got his sauce at all. The Caesar looked like it should have been served in a school lunchroom. The steak was woefully under-seasoned and certainly not worth what they charged for it.I was really disappointed with this place after reading the reviews.

I will never eat in this restaurant on a Sunday again the waitress was rude and hateful other customers were asking for silverware she couldn't even bring you rolls not to mention the food my steak wasn't cooked right they forgot to bring me my side orders the potato tasted like they cooked it last week it was hard as a rock you had to ask for everything including napkins I ordered a chicken teriyaki to go and I just wished I'd have went to Burger King instead I could have saved $138 I cannot believe I paid $17 for a little bitty piece of chicken and a half a scoop of rice and it is not what we'd call edible I am thoroughly disappointed in this restaurant and the bartender...... and by the way don't order the prime rib it has no seasoning and it is as Bland as it can be

Made a reservation a month ago for my anniversary received a message 4 days before the date of my reservation stating they are not open at the time the app allowed me to make a reservation for so my reservation was canceled. There were no other reservations available nor any offer to rectify the situation. Very disappointing service.

I’m not trying be mean because as a local, I want the locals and bourbon tourists to be able to enjoy our few sit down dinner options downtown. However, I’ve eaten here several times and the only thing I’ve ordered that is good is the burger and fries. Recently had their pasta dish with meatballs and it was baffling how anyone could make a meatball tasteless. Probably one of the worst pasta dishes I’ve ever had. The sauce was somehow tasteless and then for some reason they threw chunks of hot house winter tomatoes on top of it. We couldn’t figure out why or how this would add to the dish at all except to sear into my brain how haphazard this was. So if you’re headed there, enjoy the ambience. Enjoy the burger, but stay far away from the the pasta dish with meatballs.

So disappointing! We had a table of 4. Drinks, apps and salads were very good, all 4 us ordered burgers which was the recommendation by our server. They came out ICE cold. We sent them back, came out a second time again all 4 burgers ice cold. Manager took the burgers off our bill- but charged us for the fries that came dinner cause we “mistakingly said something nice” about the fries, by the way we did not eat the fries. Bad experience! Would highly not recommend!