Unearth The Voyage
There is a place in a small Oklahoma town where a regular evening out transforms into something you will be talking about for weeks. The setting is theatrical, the crowd is warm, and the food is the kind that makes you slow down and savor every bite.
Free live music floats through the air on multiple nights each week, and the whole experience feels more like a celebration than a casual outing. From the moment you arrive, it is clear that the people behind this spot put their whole hearts into every detail, and that energy is contagious enough to turn first-time visitors into devoted regulars.
Where to Find This One-of-a-Kind Spot
Right in the heart of Chickasha, Oklahoma, at 524 W Kansas Ave, Shakespeare Wine Company has quietly become one of the most talked-about destinations in the state. Chickasha sits about an hour south of Oklahoma City, making it an easy and rewarding road trip for anyone craving something different on a weekend.
The winery keeps a schedule that works well for evening plans. Thursday and Wednesday hours run from 4 to 9 PM, Friday and Saturday stretch from 2 to 11 PM, and Sunday wraps things up between 2 and 6 PM.
Monday and Tuesday are rest days for the crew.
You can reach them by phone at 405-825-3161 or connect through their Facebook page for the latest event updates. The building itself sits on a modest street, but once you see the warm glow coming from inside, it is hard to keep walking past without stepping in to see what all the fuss is about.
The Story Behind the Shakespeare Name
Not every winery leans into its name with this much commitment, but Shakespeare Wine Company earns every letter of that title. The entire interior is wrapped in Shakespearean decor, from theatrical touches on the walls to clever nods to the Bard that make you feel like you wandered into a literary celebration rather than a standard tasting room.
The owners, DJ and Cheri, built this place with a clear sense of personality and purpose. Their passion for crafting quality beverages shows in every bottle they produce, and their warmth as hosts turns strangers into friends within minutes of arrival.
One of the wines on the menu is even named after the owners’ daughter, carrying a distinctive lavender and dandelion finish that feels personal and poetic in equal measure. That kind of thoughtfulness runs through every part of the business, from the labels on the bottles to the way the staff greets each guest at the door.
This is not just a winery; it is a story told in sips.
A Tasting Room With Real Theatrical Flair
The first thing that hits you when you walk through the door is the atmosphere, and it delivers immediately. The space manages to feel warm and cozy without sacrificing a certain classy edge that keeps things feeling special rather than stuffy.
Mirrors line the walls in a way that adds depth and drama to the room, and the decor stays consistent with the Shakespearean theme throughout. There is even a Hall of Mirrors that leads you from the interior space out to the back patio, which is a genuinely fun transition that feels like a theatrical reveal.
The layout means there is truly no bad seat in the house. Whether you settle into a cozy corner inside or grab a picnic table on the patio under an umbrella, the vibe stays consistent and inviting.
Heated lamps on the patio make cooler evenings completely comfortable, so the outdoor experience does not disappear when the temperature drops. Every corner of this place feels intentional, and that attention to detail is part of what keeps people coming back time after time.
Live Music That Keeps the Energy High
Free live concerts happen at Shakespeare Wine Company on Thursday, Friday, and Saturday, and they are a huge part of what makes the place feel alive. The outdoor stage sits on the back patio, and the setup is intimate enough that you feel genuinely connected to the performance rather than watching from a distance.
The music lineup varies, keeping things fresh for regulars who visit multiple times each week. On any given night, you might hear acoustic folk, upbeat country, or something that blurs the lines between genres in the best possible way.
Knowing that the entertainment is included without any cover charge makes the whole evening feel like an unexpected bonus. You come for the tasting experience and stay because the music makes leaving feel like a bad idea.
The patio fills up on busy nights, so arriving a little early to claim a good spot near the stage is a smart move that pays off once the first song starts and the crowd starts to loosen up and enjoy the night.
A Wine Selection Built for Every Kind of Palate
The range of options at Shakespeare Wine Company is genuinely impressive for a boutique operation. Dry wines sit alongside sweet ones, fruity pours share shelf space with richer, fuller-bodied options, and the menu covers enough ground that even the most particular guest will find something worth savoring.
Named bottles like Wilde, Austin, and Sparky have earned loyal followings among regulars. The tasting option is especially recommended for first-time visitors, since it lets you sample across the spectrum before committing to a full glass or a bottle to take home.
Wine slushies are a crowd favorite, particularly on warm days when something cold and refreshing sounds more appealing than a traditional pour. The option to add a topper to your slushy is a small customization that people genuinely get excited about.
Whether you lean toward something light and bright or prefer a bold and complex pour, the selection here makes it easy to find your match without feeling overwhelmed by too many choices.
Food That Goes Far Beyond Bar Snacks
The food at Shakespeare Wine Company punches well above the weight of what most small wineries put on the menu. The Spinach Artichoke Dip has become something of a signature, arriving warm and satisfying in a way that makes it disappear fast from the table.
Bruschetta comes in multiple varieties, and the Mushroom and Salami version consistently gets the most enthusiastic reactions. The Strawberry Bruschetta and Avocado Bruschetta round out the options with lighter, fresher flavors that pair beautifully with the sweeter pours on the menu.
Baked Brie with honey is another standout that regulars order without hesitation, and the European-style approach to the food menu gives the whole experience a continental feel that feels unexpected in a small Oklahoma town. These are not afterthought snacks thrown together to accompany beverages.
They are thoughtfully prepared dishes that hold their own and make a strong case for building your whole evening around the table rather than just a quick tasting stop.
The Outdoor Patio Experience
The back patio at Shakespeare Wine Company deserves its own dedicated mention because it genuinely elevates the entire visit. Accessed through the Hall of Mirrors, the outdoor space opens up to picnic tables with umbrellas, a performance stage, and a relaxed layout that encourages long conversations and slow evenings.
Heated lamps are positioned throughout the space, which means the patio stays usable well into the cooler months. On a warm Oklahoma evening, there is something deeply satisfying about sitting outside under the open sky with good company and a cold wine slushy in hand.
The stage is close enough to the seating that the live performances feel personal and energetic rather than distant and performative. The whole patio has a festive quality that builds naturally as the evening progresses and more guests settle in.
Dogs are welcome in the outdoor space, which is a detail that brings a lot of smiles and makes the atmosphere even more relaxed and community-oriented for everyone who visits.
Dog-Friendly and Community-Centered
Shakespeare Wine Company has carved out a reputation as one of the most welcoming spots in the region, and the dog-friendly policy is just one example of how the owners think about inclusivity. Bringing your four-legged companion along for an evening out adds a layer of casual comfort that a lot of people genuinely appreciate.
The community aspect of this place goes deeper than pet policies, though. The owners and staff have a natural talent for making guests feel at home, and the easy conversation that flows between the team and the visitors is a consistent highlight in nearly every account of a visit here.
Locals from Chickasha and surrounding towns have embraced the winery as a gathering place, not just a tasting room. It has become the kind of spot where neighbors run into each other, where friend groups plan their Thursday nights, and where first-timers immediately start planning their return trip.
That sense of belonging is genuinely hard to manufacture, and the fact that it happens so naturally here says a lot about the people who built this place from the ground up.
The Wine Slushy You Did Not Know You Needed
Hot Oklahoma summers and wine slushies are a combination that makes complete sense once you try one at Shakespeare Wine Company. These frozen pours have become one of the most talked-about offerings on the menu, and the option to add a topper makes them even more customizable and fun.
The slushy versions are made from the same quality fruit that goes into the regular pours, so the flavor carries through even in frozen form. They are cold, refreshing, and surprisingly nuanced for something that looks like it belongs at a summer festival.
First-time visitors sometimes overlook the slushy option because they arrive focused on traditional tastings, but regulars will tell you that skipping it is a mistake worth correcting on the next visit. On a day when the Oklahoma heat is at its most relentless, a wine slushy on the shaded patio with live music playing nearby is a combination that feels almost too good to be a regular Tuesday.
Well, a regular Friday, since Tuesday is a closed day, but the sentiment stands either way.
Special Events and Creative Classes
Beyond the regular weekly schedule, Shakespeare Wine Company hosts special events that give guests even more reasons to keep coming back. Cookie decorating classes, hosted in partnership with local artists like Ashley’s Custom Cookie, bring a creative and social element to the winery experience that feels fresh and unexpected.
These events draw a crowd that might not have visited otherwise, introducing new guests to the space and the wines in a relaxed, activity-focused setting. The combination of a hands-on creative project and a welcoming atmosphere makes for an evening that feels genuinely different from a standard night out.
The owners have shown a consistent willingness to bring in outside talent and collaborate with local creatives, which keeps the event calendar varied and gives the winery a dynamic, ever-evolving personality. Checking the Facebook page before your visit is a good habit to develop, since new events get announced there first and they tend to fill up quickly once word gets out.
This is a place where something interesting is always on the horizon.
What First-Time Visitors Should Know
A few practical details can help make your first visit to Shakespeare Wine Company run as smoothly as possible. The tasting option is absolutely the right call if you are new to the menu, since it gives you a structured way to explore the range before settling on a favorite.
Arriving a bit before the live music starts on Thursday, Friday, or Saturday gives you time to get settled, order food, and find a good seat before the patio fills up. Weekend evenings in particular tend to draw a lively crowd, and the energy is noticeably higher once the music kicks in.
The staff is knowledgeable and genuinely enthusiastic about helping guests find something they will love, so do not hesitate to ask for recommendations. If you are unsure whether to lean sweet or dry, they will walk you through the options with patience and real expertise.
Coming hungry is also a smart move, since the food menu is substantial enough to anchor a full evening rather than just a quick stop. Plan to stay longer than you think you will.
Why This Oklahoma Spot Keeps Pulling People Back
There are plenty of places in Oklahoma where you can have a pleasant evening, but Shakespeare Wine Company operates on a different level of intentionality. Every element, from the Shakespearean decor to the carefully crafted menu to the free live music, feels like part of a coherent vision rather than a random collection of features.
The owners built something that reflects their personalities and their genuine love for what they do, and guests pick up on that energy immediately. People return not just for the beverages or the food but for the feeling of being in a place where the hosts actually care whether you had a good time.
For anyone based in or passing through central Oklahoma, this winery represents the kind of destination that makes you rethink what a casual night out can look like. It is proof that a small town can produce something truly exceptional when the right people pour their energy into a dream.
Shakespeare once wrote that all the world is a stage, and at this Chickasha winery, every evening feels like the opening act of something worth staying for.
