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.