Fall may be Westchester’s best season for dining.
As summer menus give way to roasted squash, apples, mushrooms, game, truffles and other richer flavors, local chefs begin creating the kinds of dinners that make an ordinary night out feel like an occasion.
This fall, Westchester diners can choose from intimate chef’s tables, multi-course tasting menus, wine-and-cheese pairings and special dinners featuring some of the area’s most accomplished chefs.
Whether you’re looking for an elaborate date night or simply want to experience a restaurant in a completely different way, here are some of the wine dinners and chef-driven culinary experiences worth knowing about this fall.
Late Harvest Five-Course Wine & Cheese Tasting – Café Deux, Harrison
September 23, 2026
One of the more intriguing early-fall events takes place at Café Deux in Harrison, where the restaurant is hosting a Late Harvest Five-Course Wine and Cheese Tasting.
The evening is built around one of autumn’s most natural pairings: wine and cheese.
Rather than a traditional dinner where wine is secondary to the food, the five-course format makes the pairing itself the experience.
For wine lovers—or anyone looking for something more interesting than a conventional Wednesday night dinner—this is exactly the kind of intimate culinary event that makes fall dining in Westchester special.
Location: Café Deux, Harrison
Date: September 23, 2026
Westchester Foodies Night – Moderne Barn, Armonk
September 16, 2026
Moderne Barn is kicking off the season with an evening designed for people who want to taste a little bit of everything.
The Armonk restaurant’s Westchester Foodies Night will feature a progression of small bites highlighting its fall menu.
The opening selections include whipped burrata with caramelized apples, butternut squash purée, toasted hazelnuts and brown butter; tuna tartare; house-made pretzel bites with cheese fondue; and meatballs with ricotta and tomato sauce.
Later bites become heartier, including orange-maple glazed duck breast, prime New York strip, miso-glazed salmon and truffle-topped pizza.
Desserts include miniature cheesecake with seasonal compote and dulce de leche bread pudding.
Wine is very much part of the evening, with a sommelier’s selection of red and white wines along with prosecco, beer and Aperol Spritzes.
It’s less formal than a seated wine dinner but perfect for someone who enjoys circulating, tasting and discovering several dishes over the course of an evening.
Location: Moderne Barn, 430 Bedford Road, Armonk
Date: September 16, 2026
Time: 6:30–8:30 p.m.
Wine Committee Dinner at Talia – Port Chester
September 17, 2026
For serious food and wine enthusiasts, one of September’s most sophisticated dinners is happening at Talia in Port Chester.
The Confrérie des Chevaliers du Tastevin’s Fairfield County chapter is holding its annual Wine Committee Dinner at the restaurant.
The evening puts the spotlight on Chef Ian Vest, whose résumé includes time at Daniel Boulud’s three-Michelin-starred DANIEL in Manhattan. Vest later became executive chef of Boulud’s DBGB Kitchen & Bar and was recognized as Most Innovative Chef at the Greenwich Wine & Food Festival.
Talia itself was recently named Best New Restaurant 2026 by Westchester Magazine.
The dinner is priced at $250 per person and is aimed squarely at diners who appreciate serious wine alongside chef-driven food.
Location: Talia, Port Chester
Date: September 17, 2026
Price: $250 per person
Beat Chef Burke – Red Horse by David Burke, White Plains
October 1, 2026
Dinner becomes a competition at Red Horse by David Burke – White Plains this October.
The restaurant is hosting another installment of its Beat Chef Burke Cooking Competition, pitting celebrity chef David Burke against guest culinary talent.
Rather than simply watching a cooking demonstration, guests sit down to a three-course dinner while the friendly competition unfolds.
Burke has built a reputation for combining serious culinary technique with a sense of theater, so the event has a somewhat livelier personality than the traditional hushed tasting-menu experience.
The October 1 dinner takes place in Red Horse’s private dining room inside The Opus Westchester.
Location: Red Horse by David Burke, 221 Main Street, White Plains
Date: October 1, 2026
Time: 6 p.m.
Price: $100 per person, plus tax and gratuity
Chef’s Table in the Wine Cellar – Apropos at The Abbey Inn, Peekskill
For one of the most intimate dining experiences in Westchester, head to The Abbey Inn.
Apropos offers a Chef’s Table inside the property’s wine cellar, creating the sort of setting normally associated with a destination resort.
The experience revolves around a chef-designed multi-course menu highlighting seasonality and culinary technique.
September’s theme is appropriately called “Harvest,” with dishes inspired by the abundance and flavors of early autumn.
Guests can add an expertly selected wine pairing for $75 or opt for a creative non-alcoholic beverage pairing for $55.
Perhaps the most appealing part is the scale: the wine cellar accommodates gatherings of up to approximately 20 guests, making the dinner feel considerably more intimate than a traditional restaurant meal.
And because you’re at The Abbey Inn, the evening can easily become an overnight fall escape overlooking the Hudson River.
Location: Apropos at The Abbey Inn, 900 Fort Hill Road, Peekskill
Wine pairing: $75 additional
September theme: Harvest
Chef’s Tasting Menu at Kanopi – White Plains
High above downtown White Plains, Kanopi The Restaurant offers one of Westchester’s most polished tasting-menu experiences.
Located on the 42nd floor, Kanopi combines dramatic views with Portuguese-influenced fine dining.
Guests looking for the full experience can choose the chef’s tasting menu, which currently starts at approximately $165 per person.
This isn’t intended to be a quick dinner. The chef-led progression can unfold over two to three hours, making it better suited to an anniversary, milestone celebration or leisurely date night.
For those who enjoy giving up control and allowing the kitchen to dictate the progression of the meal, this is one of Westchester’s true special-occasion dining experiences.
Location: Kanopi, 1 Renaissance Square, White Plains
Chef’s tasting menu: Starting at approximately $165 per person
A Michelin-Starred Tasting Menu in North Salem
One of Westchester’s most exclusive culinary experiences can be found in the quiet countryside of North Salem.
La Bastide by Andrea Calstier is an intimate Michelin-starred restaurant from Chef Andrea Calstier and Elena Oliver.
Calstier’s cooking draws heavily from his upbringing in Provence while incorporating seasonal ingredients sourced from the Hudson Valley.
Rather than an extensive à la carte menu, La Bastide is centered around a multi-course tasting experience in which the chef determines the progression of the evening.
That makes autumn an especially interesting time to visit. The restaurant’s emphasis on seasonality means the changing Hudson Valley harvest becomes part of what’s happening on the plate.
For Westchester diners who typically travel into Manhattan for Michelin-level tasting menus, this may be one of the county’s most compelling alternatives.
Location: La Bastide by Andrea Calstier, 721 Titicus Road, North Salem
Blue Hill at Stone Barns – Pocantico Hills
It’s almost impossible to discuss chef-driven dining in Westchester without mentioning Blue Hill At Stone Barns.
Located at Stone Barns Center in Pocantico Hills, the restaurant has become internationally known for Chef Dan Barber’s exploration of agriculture, sustainability and the relationship between the farm and the dinner table.
The dining experience is built around what is being grown, raised and harvested rather than a conventional list of dishes selected by the diner.
And that makes fall an especially fascinating time to experience it.
Instead of merely incorporating a few seasonal ingredients into an otherwise static menu, the agricultural landscape surrounding the restaurant helps determine what ultimately arrives at the table.
For serious food lovers, it’s less like going out for dinner and more like attending a culinary performance built around the Hudson Valley landscape.
Location: Blue Hill at Stone Barns, 630 Bedford Road, Pocantico Hills
Omakase With a Twist – Sushi by Bou, New Rochelle
Not every chef’s tasting experience needs white tablecloths and several hours.
Sushi by Bou – New Rochelle @ Westchester Place brings the Japanese omakase tradition to New Rochelle in a setting that’s considerably more playful.
Omakase essentially means putting yourself in the chef’s hands. Rather than ordering individual sushi selections, guests receive a progression of pieces chosen and prepared by the chef.
The New Rochelle location combines that tradition with a colorful, almost speakeasy-like “Disco Sushi” atmosphere.
It’s an appealing alternative for someone who wants the fun of a chef-driven tasting menu without the formality of traditional fine dining.
Location: Sushi by Bou, 40 Westchester Place, New Rochelle
An Italian Wine Night in Mamaroneck
Augustine’s Salumeria e Pasta Joint is another restaurant worth keeping on the radar as the weather cools.
The Mamaroneck restaurant from Chef Marc Taxiera and Brianne Myers takes a farm-driven approach to Italian cooking, with house-made pasta, salumi and seasonal ingredients.
It’s also notably wine-forward, making it particularly well suited to the kind of long, leisurely dinner that feels right once fall arrives.
While not every visit is structured as a formal tasting dinner, Augustine’s combination of seasonal Italian cooking and wine makes it a strong choice for diners who want to create their own fall pairing experience.
Location: Augustine’s Salumeria e Pasta Joint, 213 Halstead Avenue, Mamaroneck
Why Fall and Wine Dinners Work So Well Together
There is something about fall that lends itself particularly well to this kind of dining.
The ingredients become richer. Squash, mushrooms, apples, pears, root vegetables and late-season produce begin appearing on menus. Red wines become more appealing as evenings get cooler. Restaurants move away from the casual pace of summer and back toward longer dinners indoors.
And a tasting menu forces us to do something increasingly rare: sit down and allow dinner to unfold.
Instead of choosing an entrée, eating and leaving, you’re waiting to see what the chef sends next. A sommelier may pour a wine you would never have ordered yourself. An ingredient you normally overlook may become the best dish of the evening.
That’s part of the fun.
And this fall, you don’t need to head into Manhattan to find that experience.
Some of the region’s most interesting chef-driven dinners are happening right here in Westchester.