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.
Taste of St. Michaels
Taste of St. Michaels
Date: Saturday, November 28th
Time: TBD
Spend the Saturday after Thanksgiving tasting your way through St. Michaels. Taste of St. Michaels brings together eleven of the town’s favorite restaurants, shops and makers for an afternoon of samples and sips along Talbot Street.
Bring family and friends who are still in town for the holiday weekend and walk the historic district at your own pace. Stop in at each participating location to try a signature bite or pour, meet the people behind them, and find new favorites. It’s also Small Business Saturday, so it’s a good chance to start your holiday shopping close to home.
This year’s participants:
St. Michaels Salt Co.
Come hungry, take your time, and get a taste of what makes St. Michaels home.
More information to come.
Winter Fest in St. Michaels
Winter Fest in St. Michaels
Thursday, December 3 – Sunday, December 6
Winter Fest is back, bringing four days of holiday cheer to downtown St. Michaels.
Dine. Shop. Celebrate.
Stroll our historic streets, dressed in their winter best, and shop and dine your way through downtown. Stop by your favorite spots for special offers, festive touches, and holiday surprises all weekend long, as each business hosts its own event throughout the weekend, from cozy dinner specials to shopping deals to seasonal surprises around every corner.
Event Hours:
Thursday, December 3 | 4pm – 8pm
Friday, December 4 | 4pm – 8pm
Saturday, December 5 | 10am – 8pm
Sunday, December 6 | 10am – 2pm
Thursday, December 3
Gift of Sparkle | All day | DBS Fine Jewelers
A free jewelry cleaner with purchase.
Christmas at Guilford | Regular business hours | Guilford & Company
Christmas cookies and hot cider.
Gift of Shine | All day | Silver Linings
A free polishing cloth with purchase.
Sip, Snack and Shop | All day | The Bench Goods
Warm mulled wine, the classic bourbon and beef jerky pairing, and a taste of the High Life.
Extended Holiday Shopping Hours with Free Gift Packaging | 10am-8pm | Antiques on Talbot
Open late, with free holiday packaging on any gift purchase.
Comfort + Joy Holiday Open House | 10am-8pm | dose. wellness boutique + social spa
Tastings of chai-infused eggnog and organic teas, and a DIY holiday lotion and bath bubbles station. A free 10-minute massage with any $100+ purchase, plus a raffle for a dose. gift card.
Christmas Cocktail | 11:30am-8pm | Olive Branch
“Santa’s Little Secret,” a festive pomegranate martini.
Cheers! to Santa | 12-6pm | St. Michaels Winery
Free mulled wine tasting, a $5 glass of mulled wine, and free ginger cookies.
Hot Chocolate Bar / Milk and Cookies | 4-8pm | Arnaiz Chocolat
An outdoor hot chocolate stand with 3-4 flavors (white, traditional, mint). Inside, cones of mini chocolate chip cookies with cold milk.
It’s a “Brackish” Life Holiday Savings Days | 4-8pm | Brackish Life
Storewide sale, Locals Night, and refreshments and snacks.
Holiday Social and Raffle | 4-8pm | Olivins Tasting Room
A holiday basket raffle and photos with Ollie, plus a Locals Night with special samples and balsamic holiday mocktails.
Giveaway Basket Raffle | 4-8pm | Sea Captain’s Cottage
Christmas cookies and treats, a big blow-up Santa out front, discounts, and holiday music.
Special Sales | 4-8pm | The Christmas Shop
Sales on special merchandise.
Locals Night | 4-8pm | Book Hounds
10-20% off for locals.
Regali dall’Italia (Gifts from Italy) | 4-8pm | Simpatico, Italy’s Finest
Build your own Italian gourmet gift basket while you taste panettone and Prosecco.
Local’s Night | 4-9pm | Chesapeake Bay Outfitters
15% off regular-price merchandise, carolers in store, a gift card drawing, lite bites and libations.
Locals Night and Extended Hours | Open until 8pm | Pemberton Pharmacy & Gifts
25% off gift shop purchases (some exclusions).
Customer Appreciation Event | Open until 8pm | The Preppy Redneck
Complimentary beverages and snacks in the tent, plus discounted shopping. Every $50 spent earns a gift basket raffle entry.
Extended Hours & Ornament Booth | Open until 8pm | Treasure Cove Thrift Store
Shop late and visit the outdoor booth selling ornaments hand-crafted by local kids to help fund the new Teen Center.
Festive Holiday Experience | Dinner hours | The Galley
Dine in for a Christmas light show, letters to Santa, and a visit from Mrs. Claus and the elves. Kids eat free.
Wreath Making Class for Locals | Corah’s Corner
A holiday wreath making class. RSVP at 410-745-8008.
Friday, December 4
WinterFest Sale | All day | Charisma
Special pricing.
Gift of Sparkle | All day | DBS Fine Jewelers
A free jewelry cleaner with purchase.
Christmas at Guilford | Regular business hours | Guilford & Company
Christmas cookies and hot cider.
Gift of Shine | All day | Silver Linings
A free polishing cloth with purchase.
Sip, Snack and Shop | All day | The Bench Goods
Warm mulled wine, the classic bourbon and beef jerky pairing, and a taste of the High Life.
Extended Holiday Shopping Hours with Free Gift Packaging | 10am-8pm | Antiques on Talbot
Open late, with free holiday packaging on any gift purchase.
Comfort + Joy Holiday Open House | 10am-8pm | dose. wellness boutique + social spa
Tastings of chai-infused eggnog and organic teas, and a DIY holiday lotion and bath bubbles station. A free 10-minute massage with any $100+ purchase, plus a raffle for a dose. gift card.
Christmas Cocktail | 11:30am-8pm | Olive Branch
“Santa’s Little Secret,” a festive pomegranate martini.
Cheers! to Santa | 12-6pm | St. Michaels Winery
Free mulled wine tasting, a $5 glass of mulled wine, and free ginger cookies.
Hot Chocolate Bar / Milk and Cookies | 4-8pm | Arnaiz Chocolat
An outdoor hot chocolate stand with 3-4 flavors (white, traditional, mint). Inside, cones of mini chocolate chip cookies with cold milk.
Hot Chocolate & Cookie Stand | 4-8pm | San Miguel Restaurant
Hot chocolate, Mexican hot chocolate, and cookies.
Visiting Artist Ginger Conrad | 4-7pm | Chesapeake Bay Maritime Museum Store
Handmade oyster shell jewelry and sailboat pieces made of vintage china and sea glass from Wrackline 209. Store open until 8pm.
It’s a “Brackish” Life Holiday Savings Days | 4-8pm | Brackish Life
Storewide sale and refreshments and snacks.
Holiday Social and Raffle | 4-8pm | Olivins Tasting Room
A holiday basket raffle and photos with Ollie.
Giveaway Basket Raffle | 4-8pm | Sea Captain’s Cottage
Christmas cookies and treats, a big blow-up Santa out front, discounts, and holiday music.
Special Sales | 4-8pm | The Christmas Shop
Sales on special merchandise.
Permanent Jewelry with Charmed by Chloe | 4-8pm | Book Hounds
A permanent jewelry vendor in the shop.
Vini delle Feste (Wines for the Holidays) | 4-8pm | Simpatico, Italy’s Finest
Guided wine and food pairings. Ticketed, reservations recommended.
Prosecco & Personal Shopping | 5-9pm | Chesapeake Bay Outfitters
Prosecco tasting and lite bites. A free 10-minute massage from dose. for the first 15 customers with a purchase over $250. A portion of the proceeds goes to The Foundation for Community Development.
Sangria Mixology Class | 6-8pm | Old Brick Inn
A hands-on class with Casually Crushed LLC. Ticketed, RSVP required.
Extended Hours | Open until 8pm | Pemberton Pharmacy & Gifts
Open late for holiday shopping.
Weekend Specials & Gift Basket Raffle | Open until 8pm | The Preppy Redneck
Specials all weekend, plus a raffle entry for every $50 spent. Winner drawn Sunday afternoon.
Extended Hours & Ornament Booth | Open until 8pm | Treasure Cove Thrift Store
Shop late and visit the outdoor booth selling ornaments hand-crafted by local kids to help fund the new Teen Center.
Festive Holiday Experience | Dinner hours | The Galley
Dine in for a Christmas light show, letters to Santa, and a visit from Mrs. Claus and the elves. Kids eat free.
Live Music with Black Dog Alley | 4-7pm | Corah’s Corner
Reserve a table to guarantee live music while you dine. RSVP at 410-745-8008.
Saturday, December 5
WinterFest Sale | All day | Charisma
Special pricing.
Gift of Sparkle | All day | DBS Fine Jewelers
A free jewelry cleaner with purchase.
Christmas at Guilford | Regular business hours | Guilford & Company
Christmas cookies and hot cider.
The Vintage Christmas Photo Stop | All day | Olive Branch
A free holiday photo with a decorated vintage car, with the Classic Car Museum and San Miguel’s.
Gift of Shine | All day | Silver Linings
A free polishing cloth with purchase.
Sip, Snack and Shop | All day | The Bench Goods
Warm mulled wine, the classic bourbon and beef jerky pairing, and a taste of the High Life.
Extended Holiday Shopping Hours with Free Gift Packaging | 10am-8pm | Antiques on Talbot
Open late, with free holiday packaging on any gift purchase.
Comfort + Joy Holiday Open House | 10am-8pm | dose. wellness boutique + social spa
Tastings of chai-infused eggnog and organic teas, and a DIY holiday lotion and bath bubbles station. A free 10-minute massage with any $100+ purchase, plus a raffle for a dose. gift card.
A Little Sunshine at Flaneur | 10am-3pm | Flaneur
A pop-up with Sunshine Squares and their handcrafted Rice Krispies treats.
Grazie Mille! Customer Appreciation Day | 10am-8pm | Simpatico, Italy’s Finest
Free tastings of Italian holiday foods, wines, cheeses and antipasti all day.
Holiday Fun | 10am-6pm | Chesapeake Bay Maritime Museum Store
Raffles for CBMM prizes and surprise store discounts.
Bookish Ornament Craft | 11am-3pm | Talbot County Free Library (outside Book Hounds)
Make a book-themed ornament to take home.
Craft Your Own Ornament | 11am-3pm | San Miguel Restaurant
A DIY holiday ornament station.
Christmas Cocktail | 11:30am-8pm | Olive Branch
“Santa’s Little Secret,” a festive pomegranate martini.
Cheers! to Santa | 12-6pm | St. Michaels Winery
Free mulled wine tasting, a $5 glass of mulled wine, and free ginger cookies.
Storytime with Santa | 1-2:30pm | Book Hounds
Santa reads stories.
Hot Chocolate Bar / Milk and Cookies | 4-8pm | Arnaiz Chocolat
Hot chocolate stand with 3-4 flavors (white, traditional, mint), cones of mini chocolate chip cookies with cold milk.
Hot Chocolate & Cookie Stand | 4-8pm | San Miguel Restaurant
Hot chocolate, Mexican hot chocolate, and cookies.
It’s a “Brackish” Life Holiday Savings Days | 4-8pm | Brackish Life
Storewide sale, Santa, and refreshments and snacks.
Holiday Social and Raffle | 4-8pm | Olivins Tasting Room
A holiday basket raffle and photos with Ollie.
Giveaway Basket Raffle | 4-8pm | Sea Captain’s Cottage
Christmas cookies and treats, a big blow-up Santa out front, discounts, and holiday music.
Special Sales | 4-8pm | The Christmas Shop
Sales on special merchandise.
Permanent Jewelry with Charmed by Chloe | 4-8pm | Book Hounds
A permanent jewelry vendor in the shop.
Johnnie-O Trunk Show | 5-9pm | Chesapeake Bay Outfitters
Extra inventory and special merchandise not usually in the store. Light bites and a Lyon Rum cocktail tasting. The first 20 customers to spend $250+ get a free Johnnie-O duffle bag.
Tito’s Ugly Sweater Party | 6-9pm | Foxy’s Harbor Grille
Live music, food and drink specials, and prizes for the three ugliest sweaters.
Kocktails with Krampus | 6-10pm | Old Brick Inn
Cocktails and mischief with Eastern Shore Krampus, benefiting Toys for Tots.
Extended Hours | Open until 8pm | Pemberton Pharmacy & Gifts
Open late for holiday shopping.
Weekend Specials & Gift Basket Raffle | Open until 8pm | The Preppy Redneck
Specials all weekend, plus a raffle entry for every $50 spent. Winner drawn Sunday afternoon.
Extended Hours & Ornament Booth | Open until 8pm | Treasure Cove Thrift Store
Shop late and visit the outdoor booth selling ornaments hand-crafted by local kids to help fund the new Teen Center.
Festive Holiday Experience | Dinner hours | The Galley
Dine in for a Christmas light show, letters to Santa, and a visit from Mrs. Claus and the elves. Kids eat free.
Kids Night: Movie & Crafting | Corah’s Corner
A movie and holiday crafting night for kids. RSVP at 410-745-8008.
Sunday, December 6
Gift of Sparkle | All day | DBS Fine Jewelers
A free jewelry cleaner with purchase.
Christmas at Guilford | Regular business hours | Guilford & Company
Christmas cookies and hot cider.
The Vintage Christmas Photo Stop | All day | Olive Branch
A free holiday photo with a decorated vintage car, with the Classic Car Museum and San Miguel’s.
Gift of Shine | All day | Silver Linings
A free polishing cloth with purchase.
Sip, Snack and Shop | All day | The Bench Goods
Warm mulled wine, the classic bourbon and beef jerky pairing, and a taste of the High Life.
Extended Holiday Shopping Hours with Free Gift Packaging | 10am-4pm | Antiques on Talbot
Free holiday packaging on any gift purchase.
Comfort + Joy Holiday Open House | 10am-2pm | dose. wellness boutique + social spa
Tastings of chai-infused eggnog and organic teas, and a DIY holiday lotion and bath bubbles station. A free 10-minute massage with any $100+ purchase, plus a raffle for a dose. gift card.
Biscotti per i Cagnolini & Santa Paws | 10am-2pm | Simpatico, Italy’s Finest
Decorate doggie biscotti and get a photo with Santa Paws. A fundraiser for Baywater Animal Rescue.
Holiday Fun | 10am-6pm | Chesapeake Bay Maritime Museum Store
Raffles for CBMM prizes and surprise store discounts.
Cheers! to Santa | 10am-2pm | St. Michaels Winery
Free mulled wine tasting, a $5 glass of mulled wine, and free ginger cookies.
Christmas Cocktail | 11am-7pm | Olive Branch
“Santa’s Little Secret,” a festive pomegranate martini.
Holiday Oyster Shell Decoupage | 1-5pm | Bistro St. Michaels
Decorate oyster shell ornaments on the enclosed back patio. Ticketed, RSVP required.
Hot Chocolate Bar / Milk and Cookies | 4-8pm | Arnaiz Chocolat
An outdoor hot chocolate stand with 3-4 flavors (white, traditional, mint). Inside, cones of mini chocolate chip cookies with cold milk.
It’s a “Brackish” Life Holiday Savings Days | 4-8pm | Brackish Life
Storewide sale and refreshments and snacks.
Holiday Social and Raffle | 4-8pm | Olivins Tasting Room
A holiday basket raffle and photos with Ollie.
Giveaway Basket Raffle | 4-8pm | Sea Captain’s Cottage
Christmas cookies and treats, a big blow-up Santa out front, discounts, and holiday music.
Special Sales | 4-8pm | The Christmas Shop
Sales on special merchandise.
Gift Basket Raffle Drawing | Sunday afternoon | The Preppy Redneck
Last chance for weekend specials and raffle entries ($50 spent = 1 entry) before the winner is drawn.
Xmas Brunchin’ & Merry Mimosas | Corah’s Corner
Holiday brunch with festive mimosas. RSVP at 410-745-8008.
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.
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.
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!
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.
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.
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.
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.
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.
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.