Checkered Past Winery is the epitome of hidden gem in Dallas. The urban wine pub sits underground within the historic South Side building in the Cedars district. While the winery may be unknown to many Dallasites, Checkered Past has grown a community of loyal wine drinkers since opening their doors on Prohibition Day in 2015.
Owner and winemaker, Sandro DiSanto, instilled his wine philosophy into what Checkered Past is today, which is wine doesn't need to be a pretentious and fearsome drink even if you're not a wine expert. Wine can be a casual beverage just like beer. You can relax at a wine pub with friends and family and kick back with a glass of wine. Plenty of seating and couches at Checkered Past make for a great casual hangout spot on a Friday or Saturday night.
The urban, modern interior, designed by co-owner Scott Reylea, was completely hand built by the two - everything from the tables to the fixtures! I loved the artsy and creative atmosphere. Such a fun space to hang out!


If you're new to wine, do not fret. As Sandro says, it's all about finding what you like, and lucky for us, Checkered Past has something to match every flavor profile.
Being an advocate for the ever-growing Texas wine industry, Checkered Past carries mostly local wines. We got a taste of some of these Texas wines, as well as some made by Checkered Past's very own Sandro, using the grapes of vineyard owner and third co-owner of the trio, Carolynne Chancellor. We have to say our native state can make some pretty darn good wine! Not to mention, the highest of quality bites.
Checkered Past Winery's Tempranillo from Dallas, TX
The tempranillo was my favorite of the night. We may or may not have walked out with a couple of bottles of these!
Cheese & Charcuterie Board
Everything was SO good. They're not kidding around when they say they only serve the best. You can taste it in every part of the board. Favorites were the candied pecans and the fig preserves. You can't find these just anywhere! Trust us, we tried to find them.
Checkered Past Winery's Red Red Wine and Malbec from Dallas, TX
Smoked Salmon & Herb Cream Cheese Bruschetta
The herb cream cheese is made in-house and is heavenly.
Haak Wine's Amnesia Madeira from Galveston, TX
Cajun Pizza (available Fridays only)
Checkered Past Winery's 101 from Dallas, TX
Sticky Toffee Pudding Cake
Y'all, this cake is a MUST. It's so decadent and I cannot get enough of those candied pecans.

Be sure to sign up for the Wine Club. Every other month, Wine Club members pick up two bottles (four bottles for Level 2 members) of exclusive wines curated by Sandro. No fee to join, no cancellation fees. Your credit card will automatically be billed when you pick up your wine within the specified amount of time. Other benefits include: 10% of all wine bottles for on-site consumption, 20% off wine bottles for off-site consumption, 30% off 6 bottles or more for off-site consumption, and special invitations to winery events!
More about Checkered Past Winery here.
Thank you Checkered Past Winery for having us and comping our meal. As always, all thoughts and opinions are our own.
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