How am I 40 years old? Not sure I am okay with it, definitely don’t want to talk about it.
We were lucky enough to escape for a full 24 hours! We being me and Shane, no kids allowed. All that was set in stone was dinner and brunch reservations, the rest was…whatever the hell we wanted. We checked into our hotel room downtown about 4:00 and then to Little Italy where Brian Malarkey’s latest restaurant aka our dinner reservation was. We started at a wine bar that was packed, luckily we got ourselves a table and a nice long chat with the owner.
The weather was crap, not the day to just stroll from place to place so we needed a game plan. We booked it around the corner to Juniper and Ivy. An amazing restaurant by the brilliant Richard Blais. We cozied up with some wine and just perfect bites of food.

The worst part or maybe the best part is that I didn’t take more than two pictures. We just enjoyed the night. Looking back I wish I had, and I knew I should but the moment took over that thought, do you feel me?
After a cracking experience at Juniper we headed around the corner to Herb & Wood. The menu is so great that I struggled to choose. I ended up ordering something I would never order, lamb bolognese with fresh pasta. Not going to dive into food reviews, it was good, not great and having been to all of his restaurants I still, hands down think Herringbone is the front runner.
After dinner we Ubured ( is that even a word? ) to a “supposedly” speak easy wine bar with an Alice in Wonderland theme. The idea was fun, taking the stairs down to a grass wall that was actually a door. We sat at the bar and quickly realized it wasn’t an actual wine bar, more just a bar that had wine. The best part was the TV above us that was recording everyone coming down the outside stairs to the “hidden” doors. People are hilarious.
We moved on, now pretty good and buzzed we wandered into a bar with a live band. It was a good time but we both were ready for bed. I think we were in bed by 11:00 pm. Not bad for 40!
Our Brunch reservations were for 10:30…. I think. Wags picked us up at the hotel and we headed to Old Town to a restaurant we have never been to. The Tequila Factory, a restaurant in a hotel in the heart of Old Town. We parked underground and it really was a mess trying to find the restaurant. Once we reached the hostess she said we were 30 minutes late so we had to wait… unless we were okay with a few stairs. Shane looked to Wags’ and then back to the hostess, we told her we would be at the bar.
Finally we were seated out on the patio, the sun decided to show up. We had a good time, the food…eh, everyone else seemed to be really enjoying it.
A guitarist that has been working there for years serenaded us for a few songs, one was Stairway to Heaven because Wags.
Our bellies full we strolled through town wondering what we should do next when Old Town Saloon came into focus. An actual 21+ bar and I had never been there. We put money into the jukebox, quarters into the pool table and had a BLAST.
I used to be good at pool, really. But now I am not. Shane won every game. Bullshit! 40 is in the bag!
What a fun gataway! Lots of good food and wine. A much needed respite from children!