CBMM

St. Michaels MD

Family Funday Sunday

Historic Workboat Experience Cruises

Guided Tour: Navigating the Chesapeake

Rising Tide After-School Workshop

Van Lennep Auditorium

The Smithsonian Environmental Research Center: Ecosystem Science for the Future of the Chesapeake Bay

Yoga on Navy Point

Rosie Parks Skipjack Evening Sail

Enjoy Fabulous Italian Wines, Authentic Italian Food and Music!
Simpatico's 15th Annual Italian Wine &amp; Food Festival! Join us as we celebrate All Things Italian:
For $25 you receive:
<ul><li>Wine Tastings of up to 20 Italian wines from our Italian Importers: Cristina, Enzo, Filippo and Russ!&nbsp;</li><li>Simpatico Tasting Glass included in ticket</li><li>Food Tastings of delicious Italian specialties including Sogno Toscano Products, Cheeses, Sauces, Pestos, Olive Oil Cake, Extra Virgin Olive Oil and more</li></ul>

Local Event: Simpatico's Italy's Finest 15th Annual Italian Wine & Food Festival - 12 Noon to 4:30 PM

Talbot County

St. Michaels

Maryland

Simpatico's Italy's Finest 15th Annual Italian...

Enjoy Fabulous Italian Wines, Authentic Italian Food and Music!
Simpatico's 15th Annual Italian Wine & Food Festival! Join us...

Simpatico's Italy's Finest 15th Annual Italian Wine & Food Festival - 12 Noon to 4:30 PM

Minker Banquet Hall

Upper Shore Decoy Show Hosted by the Upper Bay Museum; celebrating our 57th year Minker Banquet Hall 920 Principio Furnace Road, Perryville Show open Saturday October 17 9am-3pm $5 general admission $10 Early Bird admission at 8am <a href="https://www.upperbaymuseum.org/decoyshow" rel="nofollow noopener" target="_blank"></a>

Local Event: Upper Shore Decoy Show

Harford County

Havre de Grace

Upper Shore Decoy Show

Upper Shore Decoy Show Hosted by the Upper Bay Museum; celebrating our 57th year  Minker Banquet Hall 920 Principio Furnace...

Join us on Oct. 24th, when we will be hosting a special Italian experience and in-shop tasting with Sisto Tessari, winemaker at his family's La Cappucina estate east of Verona in the Veneto region, with 8 wines!&nbsp; Save the date! More information and menu to come soon!&nbsp;For more information and to RVSP, click here:&nbsp;<a href="https://simpaticoshop.com/products/special-italian-experience-and-in-shop-wine-tasting-with-sisto-tessari-copy" rel="nofollow noopener" target="_blank">simpaticoshop.com/products/special-italian-experience-and-in-shop-wine-tasting-with-sisto-tessari-copy</a>

Local Event: Save the Date! Special Italian Experience and In-Shop Wine Tasting with Sisto Tessari

Save the Date! Special Italian Experience and...

Join us on Oct. 24th, when we will be hosting a special Italian experience and in-shop tasting with Sisto Tessari, winemaker at...

Save the Date! Special Italian Experience and In-Shop Wine Tasting with Sisto Tessari

Adventist HealthCare Fieldhouse

Sunday November 8, 2026

General Admission = 10am-4pm
Bringing together artisan chocolatiers, specialty coffee roasters, gourmet food vendors, and thousands of passionate attendees, this annual celebration showcases the best flavors, products, and experiences from across the region. Discover unique treats, support small businesses, and indulge in a weekend dedicated to chocolate and coffee.
Sip, Sample, and Shop from over 120 unique artisans 
Mascot Photo Opportunities, Seminars, Onsite Activities and more

Local Event: DMV Chocolate and Coffee Festival ~ Maryland Edition 

Montgomery County

Germantown

DMV Chocolate and Coffee Festival ~ Maryland...

Sunday November 8, 2026

General Admission = 10am-4pm
Bringing together artisan chocolatiers, specialty coffee roasters,...

DMV Chocolate and Coffee Festival ~ Maryland Edition 

2040 Annapolis Mall Rd, Annapolis, MD, 21401

December 4 to 6 and December 11 to 13 The festive Annapolis Holiday Market showcases about 150 local and regional artisans, offering a wide array of crafts, handmade gifts, and specialty holiday foods. Visitors can savor seasonal treats like hot chocolate and spiced wine while enjoying live entertainment and the festive holiday spirit of Annapolis. This is one of the premier holiday markets in the region and has something for everyone to enjoy. Free admission and free parking. Make it a holiday weekend to remember in Annapolis, Maryland. Tour buses welcome.

Local Event: Annapolis Holiday Market

Anne Arundel County

Annapolis

Annapolis Holiday Market

December 4 to 6 and December 11 to 13 The festive Annapolis Holiday Market showcases about 150 local and regional artisans,...

Gaby Arancibia

Baltimore Metropolitan Area

Edgewater-Davidsonville

Broadneck

Severna Park

Anne Arundel

Crofton

Prince George's County

Washington Metropolitan Area

Upper Marlboro

Kristin Danley-Greiner

Bowie

Glen Burnie

Odenton-Severn

Talbot

MD Company Solves The DIY Wedding Bar Problem

Chesapeake Bartenders and Events

If you're planning a wedding in Maryland you've probably had this conversation: "We love your bartending services, but we just can't afford $3,000." Courtney Smith, owner of Chesapeake Bartenders and Events, heard that line hundreds of times. After serving 150+ weddings across the DMV, she finally did something about it. She took everything her team does to plan seamless wedding bars and packaged it into a $99 digital guide couples can use themselves. "I got tired of watching couples stress over their wedding bar," Smith says. "They'd find some random calculator online, and I'm thinking, 'That's either way too much or not nearly enough depending on your crowd." The Real Problem: Most couples make the same mistakes: buying wrong quantities, forgetting ice melts faster in summer, not accounting for setup time, choosing glassware that breaks easily. "I've seen couples run out of alcohol at 9 PM because they used a generic calculator," Smith explains. "Or bought $500 worth of liquor they didn't need." What She Built: The DIY Wedding Bar Planning Guide includes interactive calculators that adjust for your actual wedding—time of day, season, guest demographics. It includes a 16-part audio guide and a real wedding case study showing what 155 guests consumed over five hours. The guide answers: - How much does ice melt in July vs November? - Should you buy champagne for toasts? - What's the cost difference between wine bottles and boxes? - How do you set up a bar so guests aren't waiting? Who It's For: Budget-conscious couples, couples whose venues require in-house bartending, or anyone wanting to understand what they're paying for. Smith, who has 20 years of bartending experience and runs three businesses including 1631 Event Venue, says: "Free calculators tell you what to buy. We tell you why, and how to avoid disasters." The guide is available at chesapeakebartenders.com/diy-wedding-bar-planning-guide

Bethesda-Chevy Chase

 If you're planning a wedding in Maryland you've probably had this conversation: "We love your bartending services, but we just can't afford $3,000...

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Events and Things to Do in St. Michaels, MD

Also around town...

Please confirm event details with the organizers before attending

Sunday, October 4

Tuesday, October 6

Wednesday, October 7

Thursday, October 8

Saturday, October 10

Saturday, October 17

Saturday, October 24

Sunday, November 8

Friday, December 4

Chesapeake Bartenders and Events