Ash & Olive — Restaurant in Ashland

This will be a first for me. I generally do not review in my own backyard. I spend my days delivering boxes elsewhere!

Since opening I have only heard negative comments about Ash & Olive from a few friends. The owner is unfriendly. Hmm… new restaurant, new staff, new oven, new bar… yea, I’d be a little stressed myself!!! Fear not, I have a bad habit of checking things out myself. How refreshing! At first glance, you have to take in the room. Spacious. Plenty of room for privacy and definitely wheelchair accessible. I absolutely dig the seating arrangements. A little something for any occasion.

My group of four arrived at eight. Part of our entourage had a previous not so great “experience”. We chose the couches with coffee table set up. Loved it. It’s just not something I’m used to in Ashland. Bravo! Okay… we were just there for vino and proof that Ash & Olive was doomed to failure. 😨 Oh dear… the evening was perfect. The ambiance was cool. We had a great time. Excellent wine selection. We ordered at the counter (Concept matches a great many restaurants I frequent worldwide). As I mentioned, we were just there for the vino , but one glance at the menu and I had to dive in. I ordered their Fab Four pizza. Yummy!!! The staff was fun and energetic. We did not wait on any of our orders even though all the tables were occupied.

At nine the Chris and Jeremy tag team showed up to run the now Ash & Olive Speakeasy. Nice job. We dropped the vino thing and tried a couple of cocktails recommended by Jeremy. Chris was busy checking in with all the tables. Impressive. Did I mention we live in walking distance?

Fun evening. My hats off to the owner. If you take a look at the reviews you’ll notice he answers them all. That’s another level of care and crazy. Nice!!!

If you’re in Ashland or on the ropes as to where to spend a comfortable and quaint evening, come check Ash&Olive out.

07/25/25: Another great evening at Ash & Olive. Excellent wine selection. All of our entrees were delicious, perfectly cooked. We called ahead and let them know that we were bringing our own birthday cake. They were thankful for the advance notice. All in all, another...

Ash + Olive is a gem! My new favorite restaurant. I was excited to hear about a new spot opening in downtown Ashland since options are limited, but Ash + Olive is even better than what I would have dreamed up myself. I know some are unsure about the counter service model, but we love the laidback, self-paced vibe this gives the experience. It feels like a relaxed, leisurely, tapas style meal in Europe, and the cozy couches and armchairs make you feel as comfortable as if you were in your own living room (but more glam!). You never feel rushed by waitstaff, and since we like to go out to eat for the experience and ambiance, not to get in and out in 30 minutes, it feels really unique to what other restaurants in the area offer/expect. Also, the vibe is such that you can hang out with a board game, and they have (actually good) non-alcoholic wine, beer, and cocktails, making it very family friendly. Okay, now the food: amazing! Such a refined and sophisticated menu and wine and cocktail list but without a touch of snobbery or inflated prices. The feta dip is amazing; the pizzas are amazing (we ask for less crust, which the staff generously accommodates); the orzo is so, so yum and a very generous portion. The only thing I was going to say was that I wish they had a few pasta options, and then we went again this weekend and that’s exactly what they had on the specials menu! They have lots of specials not listed on the online menu which keeps the variety fresh. Cask and Stave by Chris and Jeremy is equally amazing and such a breath of fresh air. I was in heaven being able to get such a high quality, sophisticated cocktail in our little town and to finally have a cocktail bar and an option that stays open later for those of us who eat late. So grateful to all the Ash and Olive and Cask and Stave staff for bringing these two exciting additions to...

I was so lucky to get a preview of Ash & Olive and it was an unforgettable dining experience. From the moment you walk in, you're welcomed by an ambiance that is both cozy and sophisticated – perfect for a date night or an evening out with friends. The decor combines modern elegance with warm lighting, creating a setting that’s effortlessly inviting and stylish.

The menu offers a variety of dishes that cater to all tastes. Every plate we tried was beautifully presented and packed with flavor – you can tell the chefs here are passionate about their craft. My personal favorite was the Truffle Farro & Broccolini, which had the perfect blend of spices and textures, making each bite a delight. Every ingredient tasted fresh and thoughtfully chosen, elevating each dish to new heights.

The wine and beer selection at Ash and Olive is second to none. They have an impressive range, from local craft beers to international wines, ensuring there's something to please every palate. The staff was incredibly knowledgeable, recommending the perfect wine pairing for our dishes, which really enhanced our dining experience.

Service is attentive without being intrusive, and the staff is friendly, welcoming, and clearly passionate about providing a top-notch experience. If you're looking for a spot that checks all the boxes – amazing food, exceptional drinks, and an atmosphere that feels like a little escape – Ash and Olive is the place to go. Can’t wait to come back and explore more...