As part of a trio in one venue located inside Yorktowne Social, Oak and Olive offers premier fine dining with seasonal menus and suggested wine pairings. Curious about this new place opening on Valentine's Day 2026, I easily made a reservation for dinner at 5:45 PM. Being the Grand Opening evening, I anticipated a few hiccups and found myself correct in my assumptions. I was running a bit late but called and let them know I was on my way. I arrived at 6 and was greeted inside the Social Kitchen (the main entrance). Upon checking in at the host stand I was greeted by the owner who took me to my table inside Oak and Olive. The ambiance was dark, intimate and beautiful. My table was cozy against a wall with AMAZINGLY comfortable high back chairs. A young woman approached within minutes and filled our waters and welcomed us in. Then we waited. And waited. Let the hiccups begin. Our waiter arrived at 6:30 PM. We had been waiting half an hour and joking about making a game of how long it would be before they realized we were waiting. We could have already enjoyed a few cocktails by then. Alas, Ali arrived and apologized for the delay. He seemed frazzled but when we mentioned we knew tonight was the grand opening he gave himself a pep talk right in front of us, "I've got this. I've got this." Adorable! He took our cocktail order, and we smartly went ahead and ordered our salad and entrees since we weren't sure how long those would take. The Grilled Caesar Salad (split) arrived at 6:40 and it was DELICIOUS. I would come here just to order this salad. Very, very good. Our drinks arrived ten minutes later - after we had finished the salad. Our entrees arrived at 7:40 PM. So, we've been here an hour and 40 minutes by now. Everything looked amazing. The Chilean Seabass ($52) with saffron rice and haricot verts was wonderful. Great texture, cooked to perfection, a large portion of rice and beautiful presentation on the plate. The Roseda Farm Ribeye ($58) with rainbow potatoes, broccoli rabe and a bourbon bacon cream was YUGE. Tender and smooth and very, very tasty! Paired with the Pear and Amaro Old Fashioned cocktail, it made for a delightful Valentine's dinner. I'm usually a light eater. By light I mean daylight. :) But here it was 8:30 PM and dessert was suggested by Ali so why not? A very tall and tasty piece of cheesecake arrived for us to share. From seating to leaving (6 PM to 8:45 PM), the slow service growing pains from an opening night was minimized by the beautiful ambiance, incredible food, AMAZING service by Ali (like "Muhammad Ali") and the hospitality by the owners, Ellen and Jim Trujillo. I love this concept of a fine dining, casual dining and sports bar all in one location, yet separated so you feel like you're in a totally different restaurant each time. This week I plan to try out the Sports Bar and later, the Social Kitchen. It's nice to have something so unique in the Cockeysville area, especially in the newly renovated strip mall anchored by a Food Lion and behind an IHop. Yay! I plan to be a regular. read more