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.
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.
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.
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.