When it comes to a day trip or a mini getaway excursion, people in Western New York have numerous choices if they want to combine theater with discovering wine, cider, food, and fun. There’s a nearby option that should be added to your list: Head west to the Niagara Region of Canada. Cross the bridge of your choice, either the Peace Bridge or the Lewiston-Queenston Bridge, and you’re just about there. Once you enter Canada, you can head to the flashy, sensory overload of the Niagara Falls area or go a few miles north to the more serene village of Niagara-on-the Lake (NOTL). Let’s take a right turn and head north.
What Goes Best With Wine? Try Theater With a Splash of Water
NOTL is where the flowing water of the Niagara River meets Lake Ontario. This idyllic town is pristine and exudes old-world charm. There’s an abundance of modern-yet-quaint spots to check out, including restaurants, inns, antique shops, and parks. But the ace in the hole for this town of approximately 18,000 people is one of the definitive theater organizations of North America: the Shaw Festival. The festival started in 1962, and the original goal was to present only plays by George Bernard Shaw, but they eventually expanded to include many others. As of 2026, there are three main theaters operating from spring to mid-fall (plus a few winter presentations).
We explored several of the festival's signature venues. What follows is a closer look at each stage and a select production from the current 2026 season.
Jackie Maxwell Studio Theatre
On the same lot as the much larger Festival Theatre, this 237-seat room doubles as a rehearsal space as well as a theater, thus its design is more spartan and exudes a “backstage” vibe. Because of its intimate size, you can literally sit in the first few rows (if you dare) and see the color of the actors’ eyes!
Now Playing: Bernard Shaw’s Heartbreak House (June 20 to Oct. 3)
Royal George Theatre
Dedicated in 1916, this classic 305-seat theater is near numerous restaurants and alluring stores on the town’s main street: Queen Street, which is bursting with countless plants and flowers during peak season. Due to much-needed upkeep, the theater is being renovated. Depending on the construction schedule, it will return by 2029 or sooner.
Now Playing: Anthony Shaffer’s Sleuth (April 2 to Oct. 9) Note: This production was relocated to the Court House Theatre while the Royal George Theatre is under construction.
Festival Theatre
Many early Shaw Festival plays were held at the Old Court Theatre until the 856-seat Festival Theatre debuted in 1973 and has since served as the headliner venue. The modern theater is a smart brick structure and a technically-sophisticated venue where the festival presents large-scale productions, including Broadway-worthy musicals.
Now Playing: Peter Schaffer’s Amadeus (July 8 to Oct. 4)
The Season at a Glance
As with all seasons, the 2026 season spans everything from frantic farce to deep drama. The glossy programs handed out at the start of each show are a treasure, containing background on the author, director, and setting, along with actor bios that offer a glimpse into the collective creativity that defines Shaw. Beyond the main stages, a Spiegel tent hosts cabaret-style performances and several outdoor stages are active throughout the summer. The season closes with two final productions in November and December.
Wine: Before, During, and After the Play
But wait (as they say) there’s more. The entire area has a wealth of things to do beyond the Shaw Fest and has a reputation as one of Canada’s definitive wine regions. There are approximately 40 wineries in the area with others nearby. While many establishments ask you to make a reservation, we showed up day of and were welcomed. The other thing is the fee. While they range from high to low, most charge $25 for a sparse four-wine sample. In addition, at least one winery’s website warned that you can buy a bottle from them and drink on site, but there’s a $10 corkage fee! Finally, the three we visited were flexible and courteous, but do some homework before you go.
Reif Estate Winery, 15608 Niagara Parkway
Once you pull in the driveway of this 125-acre winery, you’ll behold a spacious, opulent tasting room with rich, warm wood everywhere. Welcome to Germany. Although several other wines stood out, the Vinea caught our attention. It’s a rich and elegant port-styled wine with a premium grape-based liqueur that bursts with bright flavors of blackberry, strawberry, and cherry with red licorice notes. As the winery explains: “Cabernet Sauvignon is fortified with brandy and blended with our secret ingredients to create a one-of-a-kind 'spirit' of the vine.”
We sampled a number of wines, with ice wine being one of our favorites. Since Germany was at the forefront of making vibrant ice wines centuries ago, a German winery in Canada such as Reif truly carries on the tradition.
Southbrook Organic Vineyards, 581 Niagara Stone Road
From vast, palatial-styled chateaus straight out of a European storybook to more intimate farm-styled wineries, the look and feel of each venue varies. Designed by Jack Diamond of Diamond and Schmitt Architects, Southbrook is a true architectural standout. The visual contrast from some of the old-world style venues is dramatic. Southbrook is low and to the ground, stealth, elegant and so much more. Once you park, pedestrians cross over a streamline reflecting pool strategically placed so as to capture the glistening rays of the sun during sundown. Inside, a sleek interior dominated by glass blossoms in front of you, giving you a clear view of the vineyard. Tastings were offered in a modern lounge while, in the fair months, there’s a vast outdoor pavilion. We sat outside under a canopied tent with just a slight fall breeze greeting us.
Southbrook offers orange wines (skin-fermented white wines), specialties such as Framboise and Cassis, and Poetica (sparkling wine, rieslingdry). Although they sell “old vintage” wines, most available when we visited were from the 1990s to early 2000s. Don’t forget to check the food menu that they serve from Wednesday through Sunday, including the summer pizza charette.
Ravine Vineyard Estate Winery, 1366 York Road
It’s hard to keep up with the number of buildings on the grounds of the various wineries, like Ravine, since many wineries keep growing buildings as well as grapes. As with many other wineries, Ravine started as a family farm (in their case, at least five generations ago). There are a number of rooms you can wander in and out of: a tasting room, a mini deli with to-go items, a pizza-focused dining area, as well as a more formal restaurant area. Our table of choice on this visit was outdoors, right on the edge of the vineyard. A farm-to-table menu is available for lunch and dinner from Thursday to Sunday. And, of course, the various wines are highly recommended!
The Niagara Region for Wine, Beer, Cider and More: The U.S. side of the Niagara River
The Niagara Wine region has approximately two dozen wineries, cideries, and microbreweries but only about a dozen are officially part of the Niagara Wine Trail. As with many wine trails, it’s a great starting point when someone wants to learn more about each region. But for various reasons, many wineries choose not to become members of a trail, which is by no means an indication of quality. It often comes down to a simple business and marketing decision.
Here’s three wineries we visited recently:
Leonard Oakes Estate Winery, 10609 Ridge Road, Medina
One of the closest wineries to Rochester, on the eastern edge of the Niagara region, is Leonard Oakes in Orleans County. The casual tasting room is relatively small and almost feels like you're settling into someone's living room. White wines include riesling classic (a New York specialty) and chardonnay, while reds feature a rich red oakes, vibrant cabernet franc, and their Escape Rosé. They also offer a Steampunk Cider flight with seasonal options, popular enough that four-packs are now available.
Winery at Marjim Manor, 7171 East Lake Road, Appleton
The greeting on the winery’s web page says it best: “What is the difference between a wine and a spirit? At the Winery at Marjim Manor, wine is what you taste; spirits are who you meet.”
Housed in a reputedly haunted building that has gone through a number of changes since the 1800s, the venue is as much an experience as the wine. “As you taste our fruit and grape wines, you will hear the story about the former residents.” Wines to try include Adams Appleberry (a blend of apple and cranberry that’s “not too sweet and not too tart”), as well as gold medal winners, such as A Slice of Heaven (a sweet apple wine) and Cherry Concerto (sweet cherry). Other wines are made with peaches, plums, and pears. Whether you settle into a chair on the porch or at a table in the expansive outdoor area, open a bottle, add cheese, and relax.
Spring Lake Winery, 7373 Rochester Road, Lockport NY
The farthest west of the three wineries we visited, Spring Lake, can be discovered by following a short winding side road that dips down from the main road (Route 31) and reveals a storybook setting. The main building houses the tasting room, which stretches out to a timber lodge pavilion as well as an expansive deck hovering over an idyllic 8-acre lake. Toward the eastern edge of the water is a gazebo as well as an inviting garden grove. This winery is one of the top choices in the area for parties, fundraisers, and other events. Some of the must-try wines include their estate-grown riesling, sparkling riesling, and even a tequlia-aged riesling. As for reds, there’s a bourbon-aged syrah as well as a merlot.
A Few More Worth the Stop
There are certainly other area venues in the Niagara region, including Long Cliff Vineyards (Sanborn, NY), which is run by the third generation of the Maison Family. They host a monthly book club with stimulating conversation and (what else) wine. If you want a little bit of everything, visit Becker Farms (Gasport, NY), which celebrated its 130th anniversary in 2024. In addition to the market, Becker offers hand-crafted beers, wines, cider, and food—they even have a playground and a petting zoo.
Don’t forget to grab a bottle of wine from one of your stops. If you make it to the western edge of the region, you’ll be able to settle in, check out Niagara Falls, and open a bottle of your choice.
Fun Fact: The United States is home to at least 3,000 wineries, with at least one in every state. New York is among the leaders, with thriving wine regions stretching from Long Island in the southeast to the Niagara Trail in the northwest, and everything in between. All told, the Empire State claims an impressive share of the nation's wineries.
But for various reasons, many wineries choose not to become members of a trail, which is by no means an indication of quality.