It was a very nice experience, but not overly memorable. When we arrived, we were sat immediately as we had a reservation. Unfortunately, we were sat at a table in the very center of the dining room, which was also the very center of the flow between the rest of the restaurant and the kitchen. Our waiter, a young tall guy whose name I forget was great! He came across as being very nonchalant but the entire time we were there we never saw the man stop moving. I was very impressed. The food was fine. It was ably cooked. We both did enjoy our meals. The open kitchen is a cool concept, but when you're 30 feet away from it some cache' is lost. Everything was clean. Everything was orderly and in good repair. There really was nothing to complain about. Definitely this place is worth giving a try. It's worth the money and you may have a much more memorable experience than I. read more

Service and beverages were excellent. Beautiful space that is very inviting and welcoming. So happy we connected with friends and enjoyed a meal. They accommodated my request for veggies vs a risotto cake- much appreciated. Very disappointed with my Mahi Mahi dish- dry and not tasty. Would try one more time. Hoping for a better outcome. read more

Cypress & Oak - Espresso martini - Wine Bars Near Me - Frankfort, Kentucky

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We had an enjoyable experience with great service and tasty drinks. The food was delicious. read more

Stopped by when I was in town for a conference. Ordered the fillet which was delicious and perfectly cooked. Also just the prettiest steak I've ever seen. I couldn't decide on a sauce so the bartender (didn't catch her name but had blue hair) ordered two for me on the side! The peppercorn sauce and the garlic herb butter. Both were tasty! I Also got the fries which were perfectly crispy and salty. I would have liked them to be more truffle forward. They didn't come with a sauce which is an injustice because an aioli would take these crispy guys over the top! The vibes were nice. It was intimate in size. Cool to have the open kitchen concept. I also had the chocolate crème brûlée because I have never seen that on a menu. The bartender recommended and she didn't steer me wrong. read more

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We tried this place for brunch and were blown away! So much, that we wanted to see how their dinner was, and we were not disappointed! read more

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Wonderful atmosphere, great food, and amazing service! Our waitress was Amy and she was a joy! We didn't have to ask for a thing. She was just attentive enough but not hovering at all. We had filets and they were cooked perfectly and tasted wonderful. We ended with the Kentucky Bourbon Brown Butter cake. Wow! It was a great choice! The seating was comfortable and lighting perfect for a nice evening meal. Definitely recommend Cypress & Oak! read more

Great food and wonderful and attentive service! It was crowded when we were there but very cool vibe.

Visiting in the area, looking for nice upscale restaurant. Cypress & Oak filled the bill. Started with nice glass of chardonnay & buffalo, chicken appetizer. It was delicious came with charred toast points & carrots & celery. Plenty to share. Ordered 7oz filet with truffle herb butter, it was delicious. Perfectly cooked. Hubby had 3 huge meatballs made up of 4 different meats served with a creamy harissa sauce over linguine. It was a large portion & very good. Ordered a wedge salad to split. Very good but not so sure the bacon wasn't Oscar Meyer (real) bacon pieces. I've used them alot in a pinch, but still tasted very good. They have a nice wine list & of course lots of different bourbon. Service was excellent. Our server Jennifer was very accommodating when asked to switch tables, as the chairs weren't real comfortable. They have some comfy chairs near the bar area. Spoke with a fella named Pat, not sure his position but he was very friendly & helpful. We chatted for a few minutes. We will come back when we're back this way again Delightful dinner & food was great. It's pricier then several other restaurants in the area, but worth it. Great atmosphere. read more

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Amazing food! We had the filet mignon and truffle fries, mahi mahi with mango salsa and tomato based risotto. Compliments to the chef! Chefs kiss ‍ . The atmosphere was lovely. Our server Jessica did a fabulous job and recommended some great spots in town for us to explore for some bourbon experiences. Five stars. read more

Excellent steakhouse attached to the Delegate Hotel in Frankfort. Steaks were prepared to perfection. sides are small, usually in an upscale steakhouse the sides are large servings and offered "family style". The bar offers solid pours and the wine list is very good. I had to ding Cypress & Oak a star for the service. Goodness, they had only 2 servers for a full restaurant on a Sunday night and one of those was doing double duty as the bartender. Both were running as fast as they could, but the wait time for dinner from order to serving was long, about 45 minutes. They could have easily doubled the staff for the number of customers they had. I will give them another try on the next trip to Frankfort. read more

Stopped in for a dinner after a conference in our state capitol and immediately impressed with the classic feel of this restaurant connected to the Delegate Hotel. Really nice atmosphere and you can smell the meals being prepared combined with a smoky fragrance in the air. I had a classic Old Fashioned but smoked which made for a nice presentation. We had a very long day so we kept it simple at dinner and I had the Hangar steak which was cooked to perfection! The flavor from the steak combined with the Roasted Garlic Red Wine sauce was second to none. The shells and cheese were great also although I added salt for my taste. The server was very nice and helpful when asked about menu options. The one negative that I would say is that she needed help. At one point the restaurant seemed to be full with a few larger parties and she seemed to be the only server working. No fault of her own, so maybe they weren't expecting the crowd. That caused a few delays but we still had a great experience and dinner was amazing. Hats off to the chefs as they prepared our food wonderfully and I have to return because I didn't get the meatballs and they looked amazing! read more

Cypress & Oak - 8 oz Hangar Steak and Shells & Cheese - Wine Bars Near Me - Frankfort, Kentucky

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This place has all the hallmarks for a fantastic dining experience. Refurbished old building in the Historic district of Frankfort. Wife and i sat at the bar and both ordered a a simple old fashioned. With the exception of my drink being a solid half-inch less than my wife's, it was tasty for $13. Ordered the fritters for an appetizer. This item should be labeled as an egg roll. Fritters are fried dough with tasty bits in them. This was an egg roll wrapper filled with items that are good all by themselves, but combined taste like a salt lick. On top of that, they were ice cold. The manager graciously prepared a new one, which was nice and hot, but still too salty to eat. Let's move on to the good part. Wifey ordered filet medallions, which were perfectly cooked and well seasoned. Served with (what i hope were house made) mash potatoes and demi glaze. I ordered the cod on the recommendation of the lady sitting next to me. I NEVER order cod, because it just seems 'meh'. It was perfectly cooked and seasoned. The pea risotto was tender, and i also got a side of green beans. All perfect. There were a few setbacks. Overall, i would revisit. read more

We really loved the atmosphere at Cypress & Oak--it's a beautiful space and has a great overall vibe. Unfortunately, the food and service didn't quite meet our expectations. While it was convenient since we're staying at the connected hotel, the experience fell short enough that we wouldn't recommend it based on this visit read more

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This place is a hidden gem in downtown! Food, service and ambiance are incomparable to anything around here!! What a way to spend my birthday! read more

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The food and service was incredible. The bartender was our server and she was great. Local steak and Mac and cheese was incredible. We did the bourbon trail prior to dinner and this was nearby. We missed out on going to the sister restaurant due to it being closed on Mondays and Tuesdays. Highly recommend read more

Cypress & Oak - The ribeye and Mac and cheese - Wine Bars Near Me - Frankfort, Kentucky

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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! read more

The woman at the front was very rude. I'd give it another try, not too many spots to eat downtown Frankfort that are upscale so it's kind of disappointing that's what greeted us at the door. read more

The Service was Excellent, our Meal and dessert was Absolutely Delicious. Drinks Presented were perfect. read more

Cypress & Oak - Main Course, Retirement party. - Wine Bars Near Me - Frankfort, Kentucky

Exceptional food, service, and atmosphere. Highly recommend the cast iron skillet cod. One of the best fish dishes I've ever had. read more

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Our first time here - great service having dinner at the bar. Accommodating of allergies. Both had the salmon confit and it was delicious. A little strange that we had 8:00 reservations but they close at 9 - we didn't realize that. We enjoyed the meal a lot but some might feel rushed. We will come back - great atmosphere. read more

The food is amazing and the space is very nice. I would recommend going for a nice meal. It's not cheap but not overly expensive. The only complaint is the service is SLOOOOWWWW. They are understaffed while the mgr walks around doing nothing. Our waiter was amazing cuz she had to take orders, play bartender, deliver food, clean the tables, etc. I'm afraid that if they don't fix this staff issue they may not last. read more

This is easily the best restaurant in Frankfort and one of the best restaurants in central Kentucky. We had the meatballs and the free range chicken. The meatballs were spectacular and the chicken was the best chicken dish that my wife and I had ever tasted. The service was great, the drinks were exceptional, and the parmesan truffle tallow fries were also terrific. The Kentucky brown butter cake was delicious as dessert as well. We only live about a mile away, so we are thrilled that this restaurant is in our backyard and will be back regularly. read more

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Beautiful restaurant connecting the Delegate hotel in downtown. We had the Kentucky fritters as an appetizer which were delicious. My husband said his filet was one of the best he has ever had. The kitchen is open to the restaurant and we enjoyed the chiefs interacting with us. I believe they have only been open for a few months and are still working out some kinks with service but everyone was friendly, although maybe not the most efficient. We were not in a hurry so it was all fine. read more

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I wanted to love this place but our experience was really disappointing. Upon arriving, we were promptly seated and instantly enjoyed the vibe. However...it went downhill from there. After waiting over 25 minutes for our cocktails, we were told the smoker wasn't working. Okay, not a big deal. At the same time as ordering our drinks, we ordered an appetizer. It never came out. We later ordered our food and after waiting nearly 50 minutes, we received lukewarm warm food and were missing sides. Still no appetizer. To make it worse, while we waited 45 minutes for food, we saw numerous servers and a manager taking food from the line and eating about 15 feet away. We had hoped to speak with the manager but as we were finishing up, he seemed to already be headed out for the night. Such a disappointing overall experience. With other restaurants within walking distance, I'm not sure I'd recommend this one--especially for the elevated price point. read more

Classic American. American comfort cuisine in a tiny town our bougie boozy coffee request seemed surprising but was easily accommodated

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! read more

During our stay at The Delegate Hotel we went to dinner at Cypress & Oak and were so impressed with everything they had to offer. The food was so good I got the filet with mashed potatoes (sorry by the time I realized I should have taken a picture my plate was empty). Prices were exceptional for the quality of the foods. The drinks were so good and smooth really high quality and lastly the staff was so kind and helpful. Definitely would be sure to go back next time I am in the area. read more

I'm giving this 2 stars instead of 1 because the bartender and ambiance deserve a star. We came here on our first time out as new parents for our 1 year wedding anniversary (noted in our reservation). I ordered a blackberry cocktail and my husband ordered Blanton's, both great. We shared empanadas as an appetizer and unfortunately had to send them back because they were cold in the middle. The second replacement batch came out hot and golden as they should be. My husband ordered the meatballs as his entree which were great. I ordered the porterhouse steak medium rare with a Caesar salad. I watched the porterhouse get cut from the plastic it was in, sprayed with cooking spray and put on the grill before our appetizer was even dropped in the fryer. Safe to say, it came out medium-well. Sent it back and received it at the right temp the second time but with no salt, pepper and no fat rendering. The waitress didn't stick around or ask how the second steak was which was a red flag for the service. Hard to call this an upscale steakhouse if they can't nail a steak, I would say this is faux upscale. They have the building and local ingredients to pull off upscale but not the chef or staff to achieve it. The steak was comped but for the remaining $70 plus a tip, it wasn't worth our ruined anniversary dinner. Very sad, this is unfortunately the first time I've ever sent back a dish and for one dinner, I sent back two. read more

First time to Frankfort and ran into the best restaurant. Food was unique and spectacular! Attention to detail and full of flavor....it was top notch! We order appetizers and each one was unique and delicious. Michelin star material here! Run to this place, don't walk...you won't be disappointed read more

All I have to say is OUTSTANDING!! Top notch all around!! Food, service and specialty cocktails were amazing. A must to try while in beautiful Frankfort KY. read more

Our drink was excellent! Service was kind and welcoming. Our food was top notch! My hubs had the seafood trio with pasta and I had the meatballs with fettuccine noodles. It was elegantly made and presented. Atmosphere was cool and somewhat fancy feeling, yet we felt right at home. Lovely meal following some stops on the bourbon trail. read more

The food was absolutely delicious and the presentation was impressive. The service was slow, but we weren't in a hurry. The lighting could be a bit better. It was difficult to see the menu and the dinner. read more

Food was the best we had the whole time we were in Frankfort and some of the best I have eaten anywhere. The location is downtown and is an easy walk from any of the downtown hotels. Our waitress Jennifer was very sweet and chatted with us about the history of the place. The bar served great drinks and my whole group thoroughly enjoyed the overall atmosphere. This one is a must for that one night on your vacation that you want to have a relaxing and delicious dinner with great service!!! read more

Fantastic restaurant- as in, 12 out of 10 stars fantastic. From our server Amy offering insights on meal decisions to the chefs nailing every single thing we ordered, and the ambience to boot. This place is a complete gem! Go, you will not be disappointed! read more

Nice place. Help was impressive. But our app and wine choices weren't available. The steak was CERTAINLY not worth the price. There were mid-steps that need to be addressed. Underwhelmed. read more

We had brunch at Cypress and Oak last week while in Frankfort. Everything was fabulous - the food, the ambience, the service. Three of us ordered the avocado toast with poached eggs; we each requested eggs cooked differently, and chef got them all perfect! The accompanying skillet potatoes were also yummy. A real find in Frankfort - has only been open around 6 months for dinner, and brunch/lunch just in the past month. read more

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 easily for them. Relaxing and upscale without having to get dressed up yourself. Will absolutely be back. Well done! read more