Upcoming Events Near Trappe

Today

Sep 29, 2026

Cultural 4

4:00–8:00 Dorchester Center for the Arts Fall Art Classes -Stained Glass Dorchester Center for the Arts, 321 High Street, Cambridge, MD 21613
5:45–6:45 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
6:00–9:00 America's 250 Music Series 447 Venue, 447 Race Street, Cambridge, MD 21613
8:00–10:00 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

Tomorrow

Sep 30, 2026

Cultural 3

10:30 Garden Tours 308 Watkins Ln, Saint Michaels, MD, United States, Maryland 21663, 308 Watkins Ln, St Michaels, MD 21663-2114, United States
3:00–6:00 OCC Classic Cinema Club and the Oxford Museum Presents ‘1776’ Oxford Community Center, 200 Oxford Rd, Oxford, MD 21654, USA
5:00 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

Thursday

Oct 1, 2026

Cultural 3

7:30–9:30 Talbot Works Together Mixer The Ivy Cafe, 12 W Dover St, Easton, MD 21601, USA
5:30–8:00 Dorchester Center for the Arts Fall Art Classes -Basic Observational Drawing Dorchester Center for the Arts, 321 High Street, Cambridge, MD 21613
5:30–8:00 Dorchester Center for the Arts Fall Art Classes -Nomadic Drawing Dorchester Center for the Arts, 321 High Street, Cambridge, MD 21613

Friday

Oct 2, 2026

Cultural 7

5:00–9:00 Easton's Fall Kickoff
5:00–7:00 First Friday Gallery Walk North Harrison Street, Easton, MD, USA
5:00 First Friday Gallery Walk 11 S Harrison St, Easton, MD, United States, Maryland 21601, 11 S Harrison St, Easton, MD 21601-3042, United States
8:30 Hotel Transylvania - Outdoor Movie Night @ The Academy Art Museum (Sponsored by Framptom) 106 South Street, 106 South St, Easton, MD 21601-2917, United States
12:00–12:00 Intro to Sailing Small Craft 213 N Talbot St, St Michaels, MD
10:00–3:00 Mid-Atlantic Small Craft Festival 213 N Talbot St, St Michaels, MD
TBD Intro to Sailing Small Craft 213 N Talbot St, St Michaels, MD

Saturday

Oct 3, 2026

Cultural 11

12:00–2:00 Bookmaking Workshop & Presentation on Saturday, October 3rd, 2026 from 12-2pm at 9s Studios & Gallery 9 S Harrison St unit 9a, Easton, MD, USA
12:00 One Piece Extra Grand Battle 2026 Kent Island
1:00–4:00 The Met: Live in HD Così fan tutte by Wolfgang Amadeus Mozart The Avalon, 40 E Dover St, Easton, MD 21601-3013, United States
2:00–5:00 Live music at Foxy’s! Uncle Ward 🌴✨ 125 Mulberry St, Saint Michaels, MD, 125 Mulberry St, St Michaels, MD 21663, United States
2:30 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
6:00–6:00 A night in Madrid - Fall Fundraiser Oxford Community Center, 200 Oxford Rd, Oxford, MD 21654, USA
6:00 Gundam Card Game 1st Anniversary Event Easton
12:00–12:00 Intro to Sailing Small Craft 213 N Talbot St, St Michaels, MD
10:00–3:00 Mid-Atlantic Small Craft Festival 213 N Talbot St, St Michaels, MD
TBD Intro to Sailing Small Craft 213 N Talbot St, St Michaels, MD
12:00–12:00 Mid-Atlantic Small Craft Festival 213 N Talbot St, St Michaels, MD

Sunday

Oct 4, 2026

Cultural 6

2:00–5:00 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
3:00–4:00 Concert – The Chivalrous Crickets The Church of the Holy Trinity, 502 S Morris St, Oxford, MD 21654, USA
12:00–12:00 Intro to Sailing Small Craft 213 N Talbot St, St Michaels, MD
10:00–3:00 Mid-Atlantic Small Craft Festival 213 N Talbot St, St Michaels, MD
TBD Intro to Sailing Small Craft 213 N Talbot St, St Michaels, MD
12:00–12:00 Mid-Atlantic Small Craft Festival 213 N Talbot St, St Michaels, MD

Monday

Oct 5, 2026

Cultural 1

12:00–12:00 Mid-Atlantic Small Craft Festival 213 N Talbot St, St Michaels, MD

Tuesday

Oct 6, 2026

Cultural 4

4:00–8:00 Dorchester Center for the Arts Fall Art Classes -Stained Glass Dorchester Center for the Arts, 321 High Street, Cambridge, MD 21613
5:00–8:00 National Night Out 2026 501 Port St, Easton, MD 21601, United States
5:30–6:45 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
5:45–6:45 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

Thursday

Oct 8, 2026

Cultural 5

4:00–8:00 2nd Annual Circle of Hope Breast Cancer Awareness and Community Celebration Oxford Community Center, 200 Oxford Rd, Oxford, MD 21654, USA
5:30–8:00 Dorchester Center for the Arts Fall Art Classes -Basic Observational Drawing Dorchester Center for the Arts, 321 High Street, Cambridge, MD 21613
7:00–9:00 An Evening with The Del McCoury Band The Avalon, 40 E Dover Street, Easton, MD, United States
5:00–6:30 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
TBD 19th Annual Chesapeake Film Festival Oct 8-10 17 South Washington Street, Easton, MD, USA

Friday

Oct 9, 2026

Cultural 4

5:00–8:00 Live music at Foxy’s! Uncle Ward! 🤙🏼🌴 125 Mulberry St, Saint Michaels, MD, 125 Mulberry St, St Michaels, MD 21663, United States
7:00–9:00 Lee Fields The Avalon, 40 E Dover Street, Easton, MD, United States
5:00–6:30 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
TBD 19th Annual Chesapeake Film Festival Oct 8-10 17 South Washington Street, Easton, MD, USA

Saturday

Oct 10, 2026

Cultural 3

12:00–4:30 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
5:00–6:30 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
TBD 19th Annual Chesapeake Film Festival Oct 8-10 17 South Washington Street, Easton, MD, USA

Sunday

Oct 11, 2026

Cultural 2

7:00–9:00 David Koechner The Avalon, 40 E Dover Street, Easton, MD, United States
5:00–6:30 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

Monday

Oct 12, 2026

Cultural 1

5:00–6:30 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

Tuesday

Oct 13, 2026

Cultural 2

4:00–8:00 Dorchester Center for the Arts Fall Art Classes -Stained Glass Dorchester Center for the Arts, 321 High Street, Cambridge, MD 21613
5:00–6:30 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

Wednesday

Oct 14, 2026

Cultural 2

7:00–9:00 Oh He Dead The Avalon, 40 E Dover Street, Easton, MD, United States
5:00–6:30 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

Thursday

Oct 15, 2026

Cultural 3

5:30–8:00 Dorchester Center for the Arts Fall Art Classes -Basic Observational Drawing Dorchester Center for the Arts, 321 High Street, Cambridge, MD 21613
7:00–9:00 Antje Duvekot and Robby Hecht The Avalon, 40 E Dover Street, Easton, MD, United States
5:00–6:30 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

Friday

Oct 16, 2026

Cultural 4

5:30–7:30 Vision Board Collage with Studio Photo Portrait Session 9 S Harrison St unit 9a, Easton, MD, USA
7:00–9:00 Tyrone Vaughan The Avalon, 40 E Dover Street, Easton, MD, United States
5:00–6:30 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
9:00–4:00 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

Saturday

Oct 17, 2026

Cultural 7

12:00–5:00 Foxy’s Beer & Oyster festival ✨🦪🍻✨ 125 Mulberry St, Saint Michaels, MD, 125 Mulberry St, St Michaels, MD 21663, United States
1:00–4:00 The Met: Live in HD Macbeth by Giuseppe Verdi The Avalon, 40 E Dover St, Easton, MD 21601-3013, United States
4:30–6:30 Gather ‘Round! Community Dance 10028 Ocean Gateway, Easton, MD 21601, USA
6:00–9:00 OkSoberFest 100 Peachblossom Road, Easton, MD 21601
7:30–9:00 CREATIO EX NIHILO | Gabriela Montero 17 South Washington Street, Easton, MD, USA
5:00–6:30 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
9:00–4:00 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

Sunday

Oct 18, 2026

Cultural 2

5:00–6:30 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
9:00–4:00 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

Monday

Oct 19, 2026

Cultural 1

5:00–6:30 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

Tuesday

Oct 20, 2026

Cultural 3

4:00–8:00 Dorchester Center for the Arts Fall Art Classes -Stained Glass Dorchester Center for the Arts, 321 High Street, Cambridge, MD 21613
6:00–9:00 America's 250 Music Series 447 Venue, 447 Race Street, Cambridge, MD 21613
5:00–6:30 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

Wednesday

Oct 21, 2026

Cultural 2

5:30–7:00 Business After Hours / Ribbon Cutting: Martha's Table Martha's Table, 748 High Street at Washington St., Cambridge, MD 21613
5:00–6:30 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

Thursday

Oct 22, 2026

Cultural 3

5:30–8:00 Dorchester Center for the Arts Fall Art Classes -Basic Observational Drawing Dorchester Center for the Arts, 321 High Street, Cambridge, MD 21613
7:30–11:30 Tred Avon Players presents Ravenscroft 200 Oxford Rd, Oxford, MD
5:00–6:30 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

Friday

Oct 23, 2026

Cultural 2

7:00–9:00 Cris Jacobs & Pressing Strings A CO-BILL EVENT The Avalon, 40 E Dover Street, Easton, MD, United States
7:30–11:30 Ravenscroft - Tred Avon Players Community Theatre 200 Oxford Rd, Oxford, MD

Saturday

Oct 24, 2026

Cultural 5

9:00–12:30 Colonel Tench Tilghman Week Easton, MD, 100 W Dover St, Easton, MD 21601, USA
1:00–2:30 Spook & Paint Halloween Flower Pot Painting Workshop 9s Studios! 9 South Harrison Street, Easton, MD, USA
6:00–9:00 Live music at Foxy’s! Oliver & friends ✨ 125 Mulberry St, Saint Michaels, MD, 125 Mulberry St, St Michaels, MD 21663, United States
7:00–9:00 Amy Speace with special guest Jesse Lynn Madera The Avalon, 40 E Dover Street, Easton, MD, United States
7:30–11:30 Ravenscroft - Tred Avon Players Community Theatre 200 Oxford Rd, Oxford, MD

Sunday

Oct 25, 2026

Cultural 1

7:30–10:00 Neko Case The Avalon, 40 E Dover Street, Easton, MD, United States

Tuesday

Oct 27, 2026

Cultural 2

9:00–12:00 Poplar Island Tours Poplar Island, 21548 Chicken Point Rd, Tilghman, MD 21671, USA
4:00–8:00 Dorchester Center for the Arts Fall Art Classes -Stained Glass Dorchester Center for the Arts, 321 High Street, Cambridge, MD 21613

Upcoming events near Trappe