Conundrum Wine Bistro

I love conundrum… XOXOXO.

This is my all time favorite restaurant in Freeport. Since this restaurant opened I have yet to be disappointed with anything that I have ordered. The wine list is massive and the wines by the glass are changed each year and chosen carefully. The quality of food is high, prices reasonable. The owner Vinny is always there which is likely why the quality is so consistent and spot on. My only complaint is that Conundrum is often busy, and being a small restaurant that doesn’t take reservations this can sometimes be disappointing when you have your heart set on a cozy atmosphere and the best food and wine around. This is also not your «get in and out quickly» type of restaurant. The waitstaff and bartenders are happy to let you sample the wine and beer, they never seem put off to make sure you get something you will like, I appreciate this even if that means a longer dining experience.

We were seated promptly. The food took a while to arrive but I died order braised lamb shank… worth the wait. Our waiter was attentive. 4 stars

A wonderful experience overall. Great service, great food and a broad wine selection. The mussels were truly outstanding. Our waiter was clearly super busy but managed to provide great service.

My family loved almost all of our food (hamburger was average). The atmosphere was nice and cozy. The service was a bit lacking. It took an hour for our food to come out and that was after we questioned the wait staff about the delay.

Couldn’t have asked for more! Thank you for the customized vegan pizza that I still dream of!

Artichoke and Brie on crostini was delicious. The taste and melding of flavors was wonderful. The fish tacos were excellent and very tasty. The owner was very friendly and helpful, along with the waitstaff. I would highly recommend.

Wow! Will definitely be coming back. Our server, Shawn, was probably the best we’ve ever had — we were unsure of what wine we wanted as we’re rather inexperienced with wine — he went over a ton and gave us about 10 different tastings. We had a strawberry salad and the chicken tacos — both excellently prepared. The atmosphere is very relaxed, couches and table options with an outside deck to die for. Our desert, a chocolate burbon… Deliciousness (some pudding dish) was amazing. Our bill came out very reasonable for the quality and service we received. We will absolutely come back when we want to try some more amazing wines.

Condundrum is a good name for this charming bistro. I arrived at 6pm during the week and after a little confusion (we had a large group coming but no reservation), I selected a seat on the covered/​insulated patio. It was charming — complete with several small wood (gas maybe) stoves and comfy seating. By 7pm they were packed so I can see why they’d need the extra space.
The wine list is extensive but not especially creative or interesting. I did really appreciate the fact that they let me try two different wines before deciding — very helpful! The menu features a lot of variety — from pasta and a burger to veggie dishes, cheese plates and olives, a few salads and steak. I chose a pasta dish with butternut squash. It was meh — not really hot — but fine. Still, the portion was generous and the presentation was lovely.
Service was not great. Our server was friendly but I think she must have just been overwhelmed. Not only did water glasses go un-​filled but she never once asked if I wanted another glass of wine — and this is a wine bar! My empty plate sat on the table until after we left.
My overall impression of Conundrum is that it’s a great place for locals — I’m sure I’d go there if I lived in Freeport but I don’t think it’s worth traveling for.

Conundrum is a wine bar a little off the beaten path. I expected it to be in town Freeport where all the tourists frequent, but you have to drive a few miles out of town to get there. When you walk in the front door, there is a small bar and a few smaller intimate tables in the main room. There is also a large back room that is enclosed, but seems to be an addition added on to the main building. The group I was with sat in this back room at a large table. There were some large and small tables, as well as some wicker chairs and small fireplaces. Along the ceiling were some string lights to set the mood, although half of the string lights were burnt out. We did have to swat at a couple of mosquitos.
The major draw to this place is the huge menu. They probably have every wine or champagne you can think of, as well as some specialty cocktail drinks. You can buy by the half glass, glass, or bottle. My boyfriend and I split a bottle of prosecco for $ 20 and were happy with the quality and amount for the price. This also turned out to be a good decision because the service ended up being on the slower side. It was nice having the bottle on ice at the table so we didn’t have to wait and try to waive down our server for refills (like other people at my table had to do). Glancing at the food menu, the prices were a little higher than my liking. I expected this though for a wine bar. We did end up ordering a single cheese plate for $ 14. It was very tasty, but expensive. Again, this is what I expected for what this establishment is trying to be. However, the atmosphere was very welcoming and non-​pretentious.

«If you’re gonna be drinking, I’m gonna need to start seeing some ID’s right now.»
That was our waitress greeted us. Pretty classy, eh? No «Hi. Welcome!», no «Hello, my name is…», no «What can I start you off with?»
She then followed up it with this gem: «I don’t know what the difference between the two malbecs are. I mean, one’s from France and one’s from Argentina. Isn’t that enough of a difference for you?”*
A wine bistro who’s servers can’t tell you the difference between two drinks is a red flag. Granted she was nice enough to let us all sample as many as we wanted before making our decision, but it would have been nice if she had any knowledge about what it was she was bringing/​selling us.
Final thoughts on the service?
— And so, my experience at Conundrum is marked by pretty rough service. My companions water glasses never got filled (I actually never got ANY water); and our dirty dishes sat around until we left (the bills being placed on top of them).
Let’s talk about the vino. I had the:
— Tempranillo ($ 7) — from Spain, it was kind of a middle of the road red. You could probably drink this at a wedding or chuck it in some sangria, it’s that sort of unremarkable generic red wine.
+ Shiraz ($ 8) — from Australia, loved it! Much more sweet than I was expecting. Would definitely order this again.
— 20-​year old Tawny Port ($ 11) — I can’t believe how watery the mouthfeel on this one was and how much it blew out my palate. Make your own decision, but it wasn’t the most clean port I’ve tried.
+ Side note: I think the prices for the wine were spot on, even cheaper then some places I’ve been, so HOORAY for that!
And the food?
— Cheese Plate With Three Options ($ 24): Nope. No typo. That cheese plate with three options is a whopping $ 24. I could put something more diverse and appropriate together for cheaper at Whole Foods (and if you know the cheese prices at Whole Foods, you know that’s saying something). We had the Black Diamond Cheddar — it wasn’t cut evenly, so some slices were paper thin while others were literally over half an inch thick. Was it good? Absolutely! But the rough cuts made it difficult to properly share with another person. The Herbed Brie was the stand-​out for cheeses, though I wish it had actually been MORE herby… it seemed it was mostly for show and less for flavor. And finally we tried the bucheron which was the only one we didn’t finish because of how underwhelming it was. Also… the cheese plate came with some greens, three figs, three dried apricots, a few walnuts, some Pepperidge Farm Golden Butter Distinctive Crackers, and some baguette that smelled like popcorn. What a totally random assortment for a cheese plate.
And the ambience?
+ I think the absolute best part about Conundrum is the cozy and «wine bistro» atmosphere and ambience that they’ve created. I LOVED it. I loved the couches, and the dark red walls, and the patio with fairy lights. It was great. I could see how easy it would be to have a first date here, or a GNO (shout out to Nicole B), or dinner with the parents who are visiting from out of state.
Would I come back?
Maybe. I don’t know that I’d go out of my way for it necessarily, but if I was in the area or if someone else suggested it, I probably would.
(*Insert jokes about servers being in their own «conundrum» here)

I came into my Conundrum visit with really high expectations because 1) really high ratings and 2) a great experience at another wine bar (Carpe Diem).
I enjoyed the ambiance of the venue. We had a large group so we sat out back. There’s a variety of seating options like big chairs with a small table around a fireplace, sofas, typical dinner tables, and tables with bench seating. It all gave a warm cozy feel.
The wine list had some interesting finds. Most of the book is bottles but the glass selection was still nice. There are some wines you won’t see elsewhere like an eiswein or a wine from Greece. I had a glass of Zinfandel (forgot the brand) and it was über delicious. I recommend it if you like Zinfandels.
I had the herb Brie cheese plate and while it was yummy it definitely was not worth $ 14. The plate had slices of bread, crackers, dried apricots and figs, the cheese, and random greens. If you want more cheese (three selections) it would cost $ 26 but you don’t get extra of the bread/​crackers/​figs.
Service was painstakingly slow. Luckily we had extra glasses of water at our table for me to drink because I didn’t get a refill until over an hour into our meal. Perhaps our location in the back of the restaurant made us forgettable? If my hostess didn’t move so slowly I would have easily gotten another glass of wine or two.
I would give this establishment 2.5 stars because I have no interest in returning, but there’s some real potential in the wines you can try. Unfortunately, the poor service and exorbitant prices will likely prevent me from trying them.

Absolutely love this place. Great cozy atmosphere out back with the fireplaces. Muscles are excellent! Good wine selection. Everything I’ve ever had has been wonderful!

I looked forward to this for months– 9 months to be exact. I was excited to try this place after all the great reviews. Wow– was I disappointed! Our server was ID#177, sorry, we don’t know her name because she didn’t even take the time to introduce herself. If you knew my boyfriend and I, you would know that we are laid back and happy go lucky. She came over and threw the menus at us. She said I will be back. No introduction, no explanation, ok… We thought maybe she was just busy. Then, she came back. #177 was awful. She didn’t make eye contact, didn’t explain any wines, she hurried us to make a selection and walked off curtly. My boyfriend asked if she was okay because she seemed upset. She snapped back, «I’m fine.» We asked for the check because it wasn’t wasn’t a great experience. When she brought the check back, she said rudely, «Well, I hope your night gets better.» And we said, «We hope YOUR night gets better.» She tried to argue with us! «My night is just great, ok!» We left a tip with the note, «Sometimes you get what you don’t deserve.»
We asked for the manager and he was very nonchalant. He defended her behavior (we are convinced something else is going on… hmmm… to be that out of touch with reality) and said that he would be happy to wait on us instead. I WILL wait… for this place to close.

Fantastic. Don’t be confused by the address. It is by the giant Indian. Great ood and atmosphere. Wonderful selection of wines and beer. Don’t forget to try the dessert.

This place provides an absolutely amazing experience. We started off with some beers they had a small but solid beer list on draught. We also had a few glasses of wine. The list was long and the staff was helpful in helping us decide what we wanted. The ambiance was great. They have a L shape bar. A few high tops around the bar and some tables in the dinning room. The rest if the place included a great outside patio with comfortable patio furniture. The rest of the inside has nice sofas and places to really enjoy and relax. The drinks and ambiance was what you would expect from a good wine bistro.
What really warned this place the 5 stars were the menu and the service. The menu had excellent choices that would satisfy any pallet. There were atleast 4 entrees that I had the hardest time choosing from. It was a little overpriced but it all came together when the owner came and day with us to give us a suggestion on wine. He was extremely helpful and is exactly what an owner for any business should be!

One of our favorite stops for GNO (Girl’s Night Out, for those not connected to Urban Dictionary) even though it’s a bit out of the way.
The drinks are amazing – I can always trust to get a fabulous lemon drop here, it’s insane how many places just can’t make it right – and the food is delicious. We love to get there early enough to swipe a seat on the deck (it’s cool and breezy in the summer and toasty warm in the winter). The service is excellent, and we always have a great time.

As always, stellar service. They want you to make sure you have a drink you enjoy, even if that involves bringing you a few tastings first. There’s a wide selection of beers, wines, and cocktails. Waitstaff are very knowledgeable and can make great recommendations.
If possible, the food is even better. I can’t remember what I had here the first time but I remember it being good (either fish tacos or salmon). The second time, my food was even better. 3 out of 5 in my group ordered the pork chop. This was amazing: a perfect combination of savory and sweet. Portion was also HUGE. Should have gotten this to share. Chocolate mousse dessert was also excellent, rich (but not overly so), and smooth.
I sat outside both times. It was SO COLD the last time (plus I was just beginning to suffer from food poisoning from the weekend so I was even more miserable). Didn’t realize they could lower coverings to block out the wind for us, but they did later in the evening!

Had a group of about 16 people come here on a Friday night, and this place did not disappoint! We had our own designated waiter on back patio (nicely decorated), constantly taking drink and food orders. Appetizers were delicious — mussels, chips salsa + guac, heirloom tomatoes and goat cheese, and the cheese selection; none disappointed. Beer selection and cocktails were on point too — I’m sure a difficult thing to manage with so many people making lots of orders.
I ordered the lobster roll on croissant. So. Freaking. Good. I’m not a huge fan of the maine style, tossed with mayo, but it didn’t disappoint. The mayo wasn’t too heavy, and the croissant was buttery, soft, and altogether delicious. Salad was just some simple greens.
Would go here again in a second if back in town!

I was told I couldn’t write a review because the one time I visited, the service was having a problem and my review wouldn’t be objective for a place of this caliber. I say, call ‘em as you see ‘em. We entered on a Saturday night with no reservation at seven in the evening. We were quickly greeted by the owner who smiled and gave us a bit of a wink. He knew he didn’t have a table but said he’d check. He found us two wicker chairs and a bench on the enclosed porch next to a wood stove to occupy with drinks while we waited.
It took some time for our server to arrive but a drink order was placed. Ten minutes later our round of martinis arrived — a vesper, a Grey goose and a tanqueray up. All prepared expertly with a sheen of chipped ice floating serenely on the surface.
We ordered an assortment of cheeses ($ 26) to while the time. A 15 month cave aged cheddar, Boucher goat cheese (France) and the Stilton blue were selected as our weapons. Nearly thirty minutes later, after some prodding, they arrive. A large plate with toasted baguettes, plentiful grapes, crackers, walnuts and piles of each cheese finally emerge. Twenty six dollars is a hefty price but there included is enough to satisfy three post golf round customers.
Our «real» table is ready.
We move across the room and are seated. Round two of well made cocktails is ordered. We order dinner.
Smoked chicken ($ 19) with gravy, mac and cheese and asparagus. A ramekin stuffed with curly pasta in a light cheese sauce baked with a crispy crust is light, creamy and an excellent compliment to the smoky chicken.
The well sized chicken breast (bone in) has amazing pinkness underneath a superbly crisp skin. Moist and tender, the meat drips juice and has no need of the extra gravy. Perfect. Sweet maple or cherry chips would be my guess as for what was used to create this masterpiece of meat.
Mahi mahi fish tacos ($ 19) with sweet potato purée and cole slaw, cheese, lime and a fresh salsa are a rather pricy rendition of this western Mexican staple. Generous sized chunks of fish are grilled to flaky tender and presented upon the noted compliments.
Soy maple glaze salmon ($ 26) with mashed potatoes is the least successful of our entrees even though served at the requested med-​rare. The fish fillet comes smothered under a pile of rather standard mashed potatoes. Nothing extraordinary here as the «glaze» is virtually non existent and completely overwhelmed by the potatoes.
Given we arrived on a Saturday evening with no reservations, we shouldn’t complain about the length of our meal. The fact is, however, we were seated and ignored for ten to fifteen minutes. It took over one half hour to receive several slices of cheese. The meal in total took two and one half hours. A very lengthy meal. The chicken made it all OK. Just don’t come ravenous.