4:00 PM – 8:00 PM Dorchester Center for the Arts Fall Art Classes -Stained Glass Dorchester Center for the Arts, 321 High Street, Cambridge, MD 21613 • 21613
5:45 PM – 6:45 PM Yoga on Navy Point 213 N Talbot St, Saint Michaels, MD, United States, Maryland 21663, 213 N Talbot St, St Michaels, MD 21663-2103, United States • 21663
8:00 PM – 10:00 PM Summer Cinema on Linden Lawn 308 Watkins Ln, Saint Michaels, MD, United States, Maryland 21663, 308 Watkins Ln, St Michaels, MD 21663-2114, United States • 21663
10:30 AM Garden Tours 308 Watkins Ln, Saint Michaels, MD, United States, Maryland 21663, 308 Watkins Ln, St Michaels, MD 21663-2114, United States • 21663
3:00 PM – 6:00 PM OCC Classic Cinema Club and the Oxford Museum Presents ‘1776’ Oxford Community Center, 200 Oxford Rd, Oxford, MD 21654, USA • 21654
5:00 PM Rosie Parks Skipjack Evening Sail 213 N Talbot St, Saint Michaels, MD, United States, Maryland 21663, 213 N Talbot St, St Michaels, MD 21663-2103, United States • 21663
7:30 AM – 9:30 AM Talbot Works Together Mixer The Ivy Cafe, 12 W Dover St, Easton, MD 21601, USA • 21601
5:30 PM – 8:00 PM Dorchester Center for the Arts Fall Art Classes -Basic Observational Drawing Dorchester Center for the Arts, 321 High Street, Cambridge, MD 21613 • 21613
5:30 PM – 8:00 PM Dorchester Center for the Arts Fall Art Classes -Nomadic Drawing Dorchester Center for the Arts, 321 High Street, Cambridge, MD 21613 • 21613
5:00 PM First Friday Gallery Walk 11 S Harrison St, Easton, MD, United States, Maryland 21601, 11 S Harrison St, Easton, MD 21601-3042, United States • 21601
8:30 PM Hotel Transylvania - Outdoor Movie Night @ The Academy Art Museum (Sponsored by Framptom) 106 South Street, 106 South St, Easton, MD 21601-2917, United States • 21601
12:00 PM – 2:00 PM Bookmaking Workshop & Presentation on Saturday, October 3rd, 2026 from 12-2pm at 9s Studios & Gallery 9 S Harrison St unit 9a, Easton, MD, USA • 21601
1:00 PM – 4:00 PM The Met: Live in HD Così fan tutte by Wolfgang Amadeus Mozart The Avalon, 40 E Dover St, Easton, MD 21601-3013, United States • 21601
2:00 PM – 5:00 PM Live music at Foxy’s! Uncle Ward 🌴✨ 125 Mulberry St, Saint Michaels, MD, 125 Mulberry St, St Michaels, MD 21663, United States • 21663
2:30 PM Haunted Tales of St. Michaels 308 Watkins Ln, Saint Michaels, MD, United States, Maryland 21663, 308 Watkins Ln, St Michaels, MD 21663-2114, United States • 21663
6:00 PM – 6:00 PM A night in Madrid - Fall Fundraiser Oxford Community Center, 200 Oxford Rd, Oxford, MD 21654, USA • 21654
2:00 PM – 5:00 PM Live music at Foxy’s! Bird Dog and the Road Kings! 🎶 125 Mulberry St, Saint Michaels, MD, 125 Mulberry St, St Michaels, MD 21663, United States • 21663
3:00 PM – 4:00 PM Concert – The Chivalrous Crickets The Church of the Holy Trinity, 502 S Morris St, Oxford, MD 21654, USA • 21654
4:00 PM – 8:00 PM Dorchester Center for the Arts Fall Art Classes -Stained Glass Dorchester Center for the Arts, 321 High Street, Cambridge, MD 21613 • 21613
5:30 PM – 6:45 PM The Smithsonian Environmental Research Center: Ecosystem Science for the Chesapeake Bay's Future 213 N Talbot St, Saint Michaels, MD, United States, Maryland 21663, 213 N Talbot St, St Michaels, MD 21663-2103, United States • 21663
5:45 PM – 6:45 PM Yoga on Navy Point 213 N Talbot St, Saint Michaels, MD, United States, Maryland 21663, 213 N Talbot St, St Michaels, MD 21663-2103, United States • 21663
4:00 PM – 8:00 PM 2nd Annual Circle of Hope Breast Cancer Awareness and Community Celebration Oxford Community Center, 200 Oxford Rd, Oxford, MD 21654, USA • 21654
5:30 PM – 8:00 PM Dorchester Center for the Arts Fall Art Classes -Basic Observational Drawing Dorchester Center for the Arts, 321 High Street, Cambridge, MD 21613 • 21613
7:00 PM – 9:00 PM An Evening with The Del McCoury Band The Avalon, 40 E Dover Street, Easton, MD, United States • 21601
5:00 PM – 6:30 PM Old Point Miles River Cruise 213 N Talbot St, Saint Michaels, MD, United States, Maryland 21663, 213 N Talbot St, St Michaels, MD 21663-2103, United States • 21663
Time TBD 19th Annual Chesapeake Film Festival Oct 8-10 17 South Washington Street, Easton, MD, USA • 21601
5:00 PM – 8:00 PM Live music at Foxy’s! Uncle Ward! 🤙🏼🌴 125 Mulberry St, Saint Michaels, MD, 125 Mulberry St, St Michaels, MD 21663, United States • 21663
5:00 PM – 6:30 PM Old Point Miles River Cruise 213 N Talbot St, Saint Michaels, MD, United States, Maryland 21663, 213 N Talbot St, St Michaels, MD 21663-2103, United States • 21663
Time TBD 19th Annual Chesapeake Film Festival Oct 8-10 17 South Washington Street, Easton, MD, USA • 21601
12:00 PM – 4:30 PM Simpatico's Italy's Finest 15th Annual Italian Wine & Food Festival - 12 Noon to 4:30 PM Simpatico Italy's Finest Saint Michaels, 104 Railroad Ave, St Michaels, MD 21663, USA • 21663
5:00 PM – 6:30 PM Old Point Miles River Cruise 213 N Talbot St, Saint Michaels, MD, United States, Maryland 21663, 213 N Talbot St, St Michaels, MD 21663-2103, United States • 21663
Time TBD 19th Annual Chesapeake Film Festival Oct 8-10 17 South Washington Street, Easton, MD, USA • 21601
5:00 PM – 6:30 PM Old Point Miles River Cruise 213 N Talbot St, Saint Michaels, MD, United States, Maryland 21663, 213 N Talbot St, St Michaels, MD 21663-2103, United States • 21663
5:00 PM – 6:30 PM Old Point Miles River Cruise 213 N Talbot St, Saint Michaels, MD, United States, Maryland 21663, 213 N Talbot St, St Michaels, MD 21663-2103, United States • 21663
4:00 PM – 8:00 PM Dorchester Center for the Arts Fall Art Classes -Stained Glass Dorchester Center for the Arts, 321 High Street, Cambridge, MD 21613 • 21613
5:00 PM – 6:30 PM Old Point Miles River Cruise 213 N Talbot St, Saint Michaels, MD, United States, Maryland 21663, 213 N Talbot St, St Michaels, MD 21663-2103, United States • 21663
5:00 PM – 6:30 PM Old Point Miles River Cruise 213 N Talbot St, Saint Michaels, MD, United States, Maryland 21663, 213 N Talbot St, St Michaels, MD 21663-2103, United States • 21663
5:30 PM – 8:00 PM Dorchester Center for the Arts Fall Art Classes -Basic Observational Drawing Dorchester Center for the Arts, 321 High Street, Cambridge, MD 21613 • 21613
7:00 PM – 9:00 PM Antje Duvekot and Robby Hecht The Avalon, 40 E Dover Street, Easton, MD, United States • 21601
5:00 PM – 6:30 PM Old Point Miles River Cruise 213 N Talbot St, Saint Michaels, MD, United States, Maryland 21663, 213 N Talbot St, St Michaels, MD 21663-2103, United States • 21663
5:30 PM – 7:30 PM Vision Board Collage with Studio Photo Portrait Session 9 S Harrison St unit 9a, Easton, MD, USA • 21601
5:00 PM – 6:30 PM Old Point Miles River Cruise 213 N Talbot St, Saint Michaels, MD, United States, Maryland 21663, 213 N Talbot St, St Michaels, MD 21663-2103, United States • 21663
9:00 AM – 4:00 PM Half-Hull Modeling Workshop 213 N Talbot St, Saint Michaels, MD, United States, Maryland 21663, 213 N Talbot St, St Michaels, MD 21663-2103, United States • 21663
12:00 PM – 5:00 PM Foxy’s Beer & Oyster festival ✨🦪🍻✨ 125 Mulberry St, Saint Michaels, MD, 125 Mulberry St, St Michaels, MD 21663, United States • 21663
1:00 PM – 4:00 PM The Met: Live in HD Macbeth by Giuseppe Verdi The Avalon, 40 E Dover St, Easton, MD 21601-3013, United States • 21601
7:30 PM – 9:00 PM CREATIO EX NIHILO | Gabriela Montero 17 South Washington Street, Easton, MD, USA • 21601
5:00 PM – 6:30 PM Old Point Miles River Cruise 213 N Talbot St, Saint Michaels, MD, United States, Maryland 21663, 213 N Talbot St, St Michaels, MD 21663-2103, United States • 21663
9:00 AM – 4:00 PM Half-Hull Modeling Workshop 213 N Talbot St, Saint Michaels, MD, United States, Maryland 21663, 213 N Talbot St, St Michaels, MD 21663-2103, United States • 21663
5:00 PM – 6:30 PM Old Point Miles River Cruise 213 N Talbot St, Saint Michaels, MD, United States, Maryland 21663, 213 N Talbot St, St Michaels, MD 21663-2103, United States • 21663
9:00 AM – 4:00 PM Half-Hull Modeling Workshop 213 N Talbot St, Saint Michaels, MD, United States, Maryland 21663, 213 N Talbot St, St Michaels, MD 21663-2103, United States • 21663
5:00 PM – 6:30 PM Old Point Miles River Cruise 213 N Talbot St, Saint Michaels, MD, United States, Maryland 21663, 213 N Talbot St, St Michaels, MD 21663-2103, United States • 21663
4:00 PM – 8:00 PM Dorchester Center for the Arts Fall Art Classes -Stained Glass Dorchester Center for the Arts, 321 High Street, Cambridge, MD 21613 • 21613
5:00 PM – 6:30 PM Old Point Miles River Cruise 213 N Talbot St, Saint Michaels, MD, United States, Maryland 21663, 213 N Talbot St, St Michaels, MD 21663-2103, United States • 21663
5:30 PM – 7:00 PM Business After Hours / Ribbon Cutting: Martha's Table Martha's Table, 748 High Street at Washington St., Cambridge, MD 21613 • 21613
5:00 PM – 6:30 PM Old Point Miles River Cruise 213 N Talbot St, Saint Michaels, MD, United States, Maryland 21663, 213 N Talbot St, St Michaels, MD 21663-2103, United States • 21663
5:30 PM – 8:00 PM Dorchester Center for the Arts Fall Art Classes -Basic Observational Drawing Dorchester Center for the Arts, 321 High Street, Cambridge, MD 21613 • 21613
5:00 PM – 6:30 PM Old Point Miles River Cruise 213 N Talbot St, Saint Michaels, MD, United States, Maryland 21663, 213 N Talbot St, St Michaels, MD 21663-2103, United States • 21663
7:00 PM – 9:00 PM Cris Jacobs & Pressing Strings A CO-BILL EVENT The Avalon, 40 E Dover Street, Easton, MD, United States • 21601
7:30 PM – 11:30 PM Ravenscroft - Tred Avon Players Community Theatre 200 Oxford Rd, Oxford, MD • 21654
9:00 AM – 12:30 PM Colonel Tench Tilghman Week Easton, MD, 100 W Dover St, Easton, MD 21601, USA • 21601
1:00 PM – 2:30 PM Spook & Paint Halloween Flower Pot Painting Workshop 9s Studios! 9 South Harrison Street, Easton, MD, USA • 21601
6:00 PM – 9:00 PM Live music at Foxy’s! Oliver & friends ✨ 125 Mulberry St, Saint Michaels, MD, 125 Mulberry St, St Michaels, MD 21663, United States • 21663
7:00 PM – 9:00 PM Amy Speace with special guest Jesse Lynn Madera The Avalon, 40 E Dover Street, Easton, MD, United States • 21601
7:30 PM – 11:30 PM Ravenscroft - Tred Avon Players Community Theatre 200 Oxford Rd, Oxford, MD • 21654
9:00 AM – 12:00 PM Poplar Island Tours Poplar Island, 21548 Chicken Point Rd, Tilghman, MD 21671, USA • 21671
4:00 PM – 8:00 PM Dorchester Center for the Arts Fall Art Classes -Stained Glass Dorchester Center for the Arts, 321 High Street, Cambridge, MD 21613 • 21613