St. Michaels Business Association Sponsored
Events
Throughout the year, the SMBA hosts and sponsors signature events that draw visitors from across the region, drive excitement for our member businesses, and create the kind of memories that keep people coming back season after season.
From festive autumn weekends and holiday celebrations to community gatherings and only-in-St.-Michaels traditions, there's always something worth making the trip for.
Explore our upcoming events below and plan your next visit.
Photo Credit: Jonathan Pratt
Thursday Night Chef's’ Table Experience
Discover a new reason to visit St. Michaels every Thursday evening. Local restaurants, wineries, and taverns come together to offer exclusive chef-driven dining experiences, curated pairings, and weekly specials designed to celebrate the flavors of the Eastern Shore.
Every Thursday Night in St. Michaels!
Signature Chef-Driven Tastings
Ruse | Oysters & Bubbles Experience
Take a journey through oysters from both near and far with James Beard nominee Chef Michael Correll’s signature selections featured at Ruse’s award-winning raw bar. Sommelier Allie Balin has curated an exceptional collection of wines and bubbles from around the globe to perfectly complement the chef’s specially selected oysters.
Bistro St. Michaels | Field to Shore | A Chef’s Tasting
A weekly celebration of the Eastern Shore’s farmers, watermen, and the seasons that shape our table. Five-time readers’ choice Best Chef honoree Doug Stewart offers two to three rotating features — distinctive butcher’s cuts, locally sourced seafood, and peak-season produce — each available in limited quantities and accompanied by thoughtfully suggested wine and cocktail pairings.
The Galley Restaurant — Chef's Coastal Table
Experience a thoughtfully curated evening inspired by the Chesapeake and the West Coast vineyards that have shaped Jennifer Smith’s culinary journey. Each Thursday, Jennifer presents a rotating three-course prix fixe menu showcasing the freshest seafood, seasonal ingredients, and coastal flavors available that week.
Complementing the experience is The Galley’s carefully curated wine program, featuring many of California’s most celebrated producers, with exceptional selections available by the glass including Caymus, Cakebread, Heitz Cellar, Rombauer, and more. Suggested wine and cocktail pairings are available to enhance each course.
Intimate, candlelit, and ever-changing, Chef’s Coastal Table offers a new reason to gather in St. Michaels every Thursday evening.
Plates at 208 — Mediterranean Summer Grill Series
A weekly grilled entrée and appetizer served with salad and rice, inspired by Mediterranean summer flavors.
The Art of the Pairing
Corah’s Corner — Brews + Bites
A rotating three-course dinner thoughtfully paired with craft beer selections.
Olive Branch Mediterranean Kitchen | Greek Wine Pairing Dinner
Every Thursday in May, enjoy a three-course dinner thoughtfully paired with Greek wines — designed for sharing, savoring, and celebrating the Greek way of dining. Reservations recommended.
Simpatico, Italy's Finest | Italian Aperitivo Series
A rotating weekly experience featuring Italian red or white wines paired with savory bites inspired by different regions of Italy.
San Miguels Mexican Food — Taco Pairing for Two
Start with San Miguels’ famous Street Corn Dip to share, followed by a curated sampler of signature tacos paired with two house specialty margaritas.
Local Favorites + Weekly Specials
Theo’s — Thursday Steak Frites
Begin with Theo’s Greek Salad, followed by sliced aged New York Strip served with pub sauce and fries, finished with cheesecake for two.
Gina’s Cafe — Elevated Coastal Flavor
Gina's Cafe transforms Thursday evenings with exclusive Chefs' Table offerings. Come experience their deep love for fresh avocados and vibrant coastal ingredients through beautifully crafted, rotating weekly specials in a welcoming, uniquely local atmosphere.
Ava’s Pizzeria & Wine Bar — 3-Course Pasta Night
Start with a Caesar salad, followed by rigatoni in spicy vodka sauce with house-made mozzarella, fresh basil, and parmesan, finished with warm beignets.
Foxy’s Harbor Grille — Harborside Seafood Selections
Experience an intimate taste of the shoreline with exclusive, seasonal seafood menus curated by our culinary team, featuring ingredients at their absolute peak.
Talbot Street Tavern | Thursday Sushi Experience
An elevated sushi evening featuring a rotating selection of sushi and nigiri rolls.
Sip + Socialize
St. Michaels Winery | Weekly Wine Spritzer Feature
Enjoy a refreshing seasonal wine spritzer with flavors changing weekly.
Pursers Pub | “Goodnight Kiss” Cocktail Feature
A signature cocktail inspired by the final hole of the Links Golf Course at Inn at Perry Cabin.
Reservations are highly encouraged as many of these chef-driven specials are produced in limited quantities throughout the season.
Community Harvest Supper
One table. One community.
An evening rooted in the bounty of the Eastern Shore, Community Harvest Supper brings together a culinary alliance of St. Michaels' finest chefs and local farmers around one extraordinary table. The evening unfolds with a welcoming reception, family-style feast, silent and live auctions, live music, and dancing, all in celebration of the food, people, and community that make our region so special.
Join us for the inaugural gathering, held in support of the institutions that hold St. Michaels together: the Community Garden, Community Center, and Farmers Market.
Sunday, September 20, 2026
3:00pm
Inn At Perry Cabin
Farmer Formal Attire
This year marks the very first Community Harvest Supper. Reserve your place at the table.
Tickets and full details:
https://innatperrycabin.ticketspice.com/community-harvest-supper
For general ticket and event information, contact Vincent Savignano at
Vincent.Savignano@innatperrycabin.com.
For sponsorship inquiries, contact Amy Horne at
AmyH@stmichaelscc.org or 410-745-6073 ext. 1.
Fall Into St. Michaels
Fall Into St. Michaels is the Eastern Shore's most spirited autumn celebration — a full weekend of seasonal fun, festive flavors, and small-town charm that makes October in St. Michaels something truly special. No tickets, no hassle, just pure fall magic woven into every corner of our historic waterfront town.
Yappy Hour at Foxy’s!
Kick off Fall Into St. Michaels with Yappy Hour at Foxy's Harbor Grille! Grab a drink, bring your pup, and settle in on Foxy’s patio to start the Eastern Shore's most spirited autumn celebration the right way.
Petals & Pumpkins Floral Arrangement Class
Petals & Pumpkins returns to Corah's Corner on Friday, October 16th from 6-9 PM under the pergola. Craft your own pumpkin flower centerpiece with fresh local blooms, sip three featured fall cocktails, and enjoy a cozy evening of fall fun with giveaways throughout the night. $60, family pricing available, space is limited.
Pumpkin Carving
Watch master carvers bring jack-o-lanterns to life at Pumpkin Carving, Saturday, October 17th at St. Luke's Parish Hall. Public viewing runs 9am-noon and 1-7pm (closed briefly for judging), with a chance to tour the finished themed creations and meet the carvers behind them.
Children’s Pumpkin Painting and Face Painting
Kids can paint their own pumpkin to take home and get their face painted at Children's Pumpkin Painting and Face Painting, Saturday, 11am-1pm at the St. Michaels Community Center. Free event, brought to you by the St. Michaels Police Department and SMYLE.
Pumpkin Baking Contest
Sample sweet pumpkin creations from local bakers at the Pumpkin Baking Contest, judging begins at 11am at the St. Michaels Community Center. Buy a slice or the whole pie, with proceeds benefiting the Community Center.
Children’s Storytelling
Get in the Halloween spirit with kid-friendly, themed stories at Children's Storytelling, 11am at Book Hounds, brought to you by your local independent bookstore.
The 4th Annual Wag-O-Ween Costume Contest
Dress up your pup and hit the streets for trick-or-treating at the 4th Annual Wag-O-Ween Costume Contest, noon-3pm, meeting in the parking lot behind The Preppy Redneck. Costume prizes awarded, $10 entry with proceeds benefiting Talbot County Humane Society.
Foxy’s Second Annual Beer & Oyster Garden
Sip seasonal beers and cocktails while enjoying oysters prepared every which way at Foxy's Second Annual Beer and Oyster Garden, noon-5pm at Foxy's Harbor Grille & Lu's at the Marina. A shore delight!
Pumpkin Viewing
The viewing follows the Pumpkin Carving contest, once the carvers have finished their work and judging has wrapped up. Stop by to tour the collection of themed jack-o-lanterns on display and see this year's winning creations up close.
Jack Russell Races
The St. Michaels Jack Russell Races are an annual event that is a blast for dogs, their owners, and onlookers alike. Packed with dogs, big and small the races take place at the St. Michaels Inn and support local charities like Talbot Humane, Baywater Animal Rescue and Caroline County Humane Society.
Midnight Madness
Midnight Madness is St. Michaels' most beloved holiday tradition — a one-night celebration that transforms our charming waterfront town into a glittering, festive experience unlike anything else on the Chesapeake. Shops and boutiques stay open late with exclusive holiday specials, live music fills the streets, and fire pits and holiday lights set the scene for an unforgettable evening of small-town Christmas magic.
2026 Independence Day Decorating Contest
Calling all St. Michaels residents and visitors - the St. Michaels Business Association is asking for your participation. Each business in town will be decorated for the semiquincentennial, and we are asking for your vote.
As a participant you will be able to register via QR code located in each of the participating businesses. As you walk through town take notice to see which one you like the best. When you register you will be entered into a drawing on July 5 for a gift basket supplied by participating businesses.
You do not need to be present to win. We hope to see you out and about and let’s have a great celebration this Fourth of July.
Gift Basket Prize Pack
St. Michaels ChocolateFest
Indulge in the sweetest weekend of the year! The 8th Annual St. Michaels ChocolateFest returns on Saturday, March 7, 2026, inviting chocolate lovers from near and far to savor an unforgettable day of decadent delights. Throughout town, restaurant chefs will showcase limited-edition, chocolate-inspired dishes and desserts, while local shops and tasting rooms offer tempting treats, artisan confections, wine, beer, spirits, and more.