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October 2026
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Events for October 2026
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4 ongoing events
in the week of September 27
Advantages of Services in AHD Clinic
Creative Circle – Monthly Meetup (2026)
Registration for Theater Classes Now Open – All Ages
English Dance to delightful live music, excellent callers and friendly community
See them in the list
Sunday, September 27
27
, September 2026, 28 events
September 27:
Wellness Day Retreat at The Happy Seed Meditation Gardens
September 25 – September 27:
All Things Go Music Festival
September 25 – September 30:
★
Featured:
Garden Chores & Coffee: Seed & Feed Your Lawn
September 27,
11:00 am – 3:00 pm
★
Featured:
Sparks & McCoy
September 27,
4:00 pm – 7:00 pm
★
Featured:
Mike Heuer
September 27,
8:00 am – 5:00 pm
St. Mary’s County Fair
+ 22 More
events on September 27, 2026
Monday, September 28
28
, September 2026, 4 events
September 25 – September 30:
Garden Chores & Coffee: Seed & Feed Your Lawn
September 28,
9:00 am – 5:00 pm
AACS Athletic Golf Classic
September 28,
8:00 pm – 10:00 pm
Michael Franti Trio w/ Wheeland Brothers
September 28,
10:00 pm – 12:00 am
Midnight Release Party: Threshing Day
Tuesday, September 29
29
, September 2026, 4 events
September 29:
Tunesday: A Floating Concert Series
September 25 – September 30:
Garden Chores & Coffee: Seed & Feed Your Lawn
September 29,
7:30 pm – 8:30 pm
Staged Reading of “Writing in Diners”
September 29,
8:00 pm – 10:00 pm
Los Lonely Boys
Wednesday, September 30
30
, September 2026, 4 events
September 25 – September 30:
Garden Chores & Coffee: Seed & Feed Your Lawn
September 30,
10:00 am – 11:00 am
★
Featured:
Fall to Spring Container Garden
September 30,
5:00 pm – 8:00 pm
Chapman Farm Food Truck Wednesdays
September 30,
5:00 pm – 10:00 pm
Dinner Under the Stars
Thursday, October 1
1
, October 2026, 9 events
October 1,
4:00 pm – 7:00 pm
★
Featured:
Anthony Frijia
October 1,
5:00 pm – 7:00 pm
Teachers’ Night Out
October 1,
5:30 pm – 8:00 pm
End of Summer Luau
+ 6 More
events on October 1, 2026
Friday, October 2
2
, October 2026, 14 events
October 2 – October 7:
★
Featured:
Garden Chores & Coffee: Plant Fall Annuals & Divide Perennials
October 2,
2:00 pm – 7:00 pm
★
Featured:
Michael McHenry
October 2,
8:00 am – 8:00 pm
Gold’s Gym invites communities nationwide to work out for free during First Friday Free Workout activation
October 2,
9:00 am – 10:30 am
Annapolis Lower School Parent Preview Day
+ 10 More
events on October 2, 2026
Saturday, October 3
3
, October 2026, 31 events
October 3:
Fall Saturdays at Ridge Grow
October 2 – October 7:
Garden Chores & Coffee: Plant Fall Annuals & Divide Perennials
October 3,
11:00 am – 3:00 pm
★
Featured:
B.en
October 3,
8:00 am – 12:00 pm
The Stable Strength & Conditioning Grand Opening
October 3,
10:00 am – 11:30 am
Lower Body Fascial Maneuvers Class
+ 26 More
events on October 3, 2026
4 ongoing events
in the week of October 4
Advantages of Services in AHD Clinic
Creative Circle – Monthly Meetup (2026)
Registration for Theater Classes Now Open – All Ages
English Dance to delightful live music, excellent callers and friendly community
See them in the list
Sunday, October 4
4
, October 2026, 22 events
October 4:
Lifeline 100 Bicycle Event
October 4:
(Extended!) You’re a Good Man, Charlie Brown – Presented by Compass Rose Theater
October 2 – October 7:
★
Featured:
Garden Chores & Coffee: Plant Fall Annuals & Divide Perennials
October 4,
10:00 am – 12:00 pm
★
Featured:
Kids’ Club Workshop – Spooky Pumpkin Decorating
October 4,
12:00 pm – 3:00 pm
★
Featured:
The Grilled Lincolns
October 4,
12:00 pm – 4:00 pm
★
Featured:
Paint Your Pet Night – Severna Park
+ 16 More
events on October 4, 2026
Monday, October 5
5
, October 2026, 7 events
October 5:
Annie Awards
October 2 – October 7:
Garden Chores & Coffee: Plant Fall Annuals & Divide Perennials
October 5,
5:30 pm – 8:00 pm
★
Featured:
Mahjong 101 | Beginner Class – Beer Farm
October 5,
5:00 pm – 7:30 pm
Busch Annapolis Library Fall Film Series: Alfred Hitchcock – Master of Suspense
October 5,
6:00 pm – 7:00 pm
Retire on Purpose
+ 2 More
events on October 5, 2026
Tuesday, October 6
6
, October 2026, 3 events
October 2 – October 7:
Garden Chores & Coffee: Plant Fall Annuals & Divide Perennials
October 6,
6:00 pm – 8:00 pm
★
Featured:
Mahjong Social Play – Beer Farm
October 6,
8:00 pm – 10:00 pm
Lynch Mob
Wednesday, October 7
7
, October 2026, 5 events
October 2 – October 7:
Garden Chores & Coffee: Plant Fall Annuals & Divide Perennials
October 7,
10:00 am – 11:00 am
★
Featured:
October Magic in the Garden
October 7,
9:00 am – 10:30 am
Severn Lower School Parent Preview Day
October 7,
5:00 pm – 8:00 pm
Chapman Farm Food Truck Wednesdays
+ 1 More
events on October 7, 2026
Thursday, October 8
8
, October 2026, 10 events
October 8,
5:00 pm – 8:00 pm
★
Featured:
Bob Krauss and Warren Prentice
October 8,
10:00 am – 6:30 pm
Annapolis Powerboat Show
October 8,
10:00 am – 6:30 pm
Annapolis Powerboat Show
+ 7 More
events on October 8, 2026
Friday, October 9
9
, October 2026, 17 events
October 9,
10:00 am – 11:00 am
★
Featured:
Rethinking & Embracing Edibles
October 9,
4:00 pm – 7:00 pm
★
Featured:
Michael McHenry
October 9,
10:00 am – 6:30 pm
Annapolis Powerboat Show
+ 14 More
events on October 9, 2026
Saturday, October 10
10
, October 2026, 39 events
October 10:
Fall Saturdays at Ridge Grow
October 10,
11:00 am – 3:00 pm
★
Featured:
Michael McHenry
October 10,
4:00 pm – 7:00 pm
★
Featured:
The Wombmates
October 10,
7:00 am – 3:00 pm
Country Fair Day
+ 35 More
events on October 10, 2026
5 ongoing events
in the week of October 11
Advantages of Services in AHD Clinic
Creative Circle – Monthly Meetup (2026)
Registration for Theater Classes Now Open – All Ages
English Dance to delightful live music, excellent callers and friendly community
English Dance to delightful live music, excellent callers and friendly community
See them in the list
Sunday, October 11
11
, October 2026, 30 events
October 11,
11:00 am – 3:00 pm
★
Featured:
Dan Haas
October 11,
4:00 pm – 7:00 pm
★
Featured:
Jason Bishop
October 11,
9:00 am – 5:00 pm
Catoctin Colorfest
+ 27 More
events on October 11, 2026
Monday, October 12
12
, October 2026, 4 events
October 12,
5:30 pm – 8:00 pm
★
Featured:
Mahjong 101 | Beginner Class – The Gardens
October 12,
5:00 pm – 7:30 pm
Busch Annapolis Library Fall Film Series: Alfred Hitchcock – Master of Suspense
October 12,
7:30 pm – 9:30 pm
October Cabaret
+ 1 More
events on October 12, 2026
Tuesday, October 13
13
, October 2026, 4 events
October 13,
6:00 pm – 7:00 pm
Health Savings Accounts
October 13,
6:00 pm – 7:00 pm
Health Savings Accounts
October 13,
7:00 pm – 8:30 pm
Brothers in Arms: The Revolutionary Service of James and Edmund Brice
+ 1 More
events on October 13, 2026
Wednesday, October 14
14
, October 2026, 8 events
October 14,
10:00 am – 11:00 am
★
Featured:
Garden Chores & Coffee: Plant Trees, Shrubs, & Perennials
October 14,
10:00 am – 11:00 am
★
Featured:
Inspiration for Your Fall Garden
October 14,
8:30 am – 11:00 am
BoardMatch
+ 5 More
events on October 14, 2026
Thursday, October 15
15
, October 2026, 16 events
October 15,
4:00 pm – 8:00 pm
★
Featured:
Dan Haas
October 15,
5:30 pm – 8:00 pm
★
Featured:
Mahjong 102 | Guided Play – The Gardens
October 15,
9:00 am – 12:00 pm
AACS Middle School Visit Days
+ 13 More
events on October 15, 2026
Friday, October 16
16
, October 2026, 11 events
October 16 @ 7:30 pm – October 18 @ 9:30 pm:
La Sylphide
October 16,
4:00 pm – 7:00 pm
★
Featured:
Michael McHenry
October 16,
9:00 am – 5:00 pm
#22FORYOU Day
October 16,
10:00 am – 6:30 pm
Annapolis Sailboat Show
+ 7 More
events on October 16, 2026
Saturday, October 17
17
, October 2026, 34 events
October 17:
Inaugural Harvest Gala
October 17 @ 10:00 am – October 18 @ 4:00 pm:
Art @ the Park
October 16 @ 7:30 pm – October 18 @ 9:30 pm:
La Sylphide
October 17,
11:00 am – 3:00 pm
★
Featured:
Doug Segree
October 17,
4:00 pm – 7:00 pm
★
Featured:
Mike Heuer
October 17,
8:00 am – 2:00 pm
B.I.G. Book Sale
+ 28 More
events on October 17, 2026
5 ongoing events
in the week of October 18
Advantages of Services in AHD Clinic
Creative Circle – Monthly Meetup (2026)
English Dance to delightful live music, excellent callers and friendly community
English Dance to delightful live music, excellent callers and friendly community
First Exposure: Beginner Photography (4- week workshop)
See them in the list
Sunday, October 18
18
, October 2026, 14 events
October 17 @ 10:00 am – October 18 @ 4:00 pm:
Art @ the Park
October 16 @ 7:30 pm – October 18 @ 9:30 pm:
La Sylphide
October 18,
11:00 am – 3:00 pm
★
Featured:
One Night Only Band
October 18,
4:00 pm – 7:00 pm
★
Featured:
Anthony Frijia
October 18,
10:00 am – 4:00 pm
Art @ the Park 2026
+ 9 More
events on October 18, 2026
Monday, October 19
19
, October 2026, 3 events
October 19,
5:00 pm – 7:30 pm
Busch Annapolis Library Fall Film Series: Alfred Hitchcock – Master of Suspense
October 19,
6:00 pm – 7:00 pm
Social Security – Understanding the Ins and Outs of Social Security
+ 1 More
events on October 19, 2026
Tuesday, October 20
20
, October 2026, 4 events
October 20,
5:30 pm – 8:00 pm
★
Featured:
CA$H BA$H
October 20,
5:30 pm – 8:00 pm
★
Featured:
Mahjong 101 | Beginner Class – The Gardens
October 20,
6:30 pm – 9:00 pm
Caymus Vineyards Wine Dinner at Stoney River
+ 1 More
events on October 20, 2026
Wednesday, October 21
21
, October 2026, 3 events
October 21,
10:00 am – 11:00 am
★
Featured:
Fall in Love with Birding
October 21,
5:30 pm – 8:00 pm
★
Featured:
Mahjong 101 | Beginner Class – The Gardens
+ 1 More
events on October 21, 2026
Thursday, October 22
22
, October 2026, 2 events
October 22,
4:00 pm – 7:00 pm
★
Featured:
Joey Fitz
October 22,
6:00 pm – 7:00 pm
★
Featured:
Salty Girls Books x Homestead Gardens Book Club
Friday, October 23
23
, October 2026, 6 events
October 23 – October 28:
★
Featured:
Garden Chores & Coffee: Houseplant Care for Fall & Winter
October 23,
4:00 pm – 7:00 pm
★
Featured:
Michael McHenry
October 23,
1:00 pm – 4:00 pm
Narrative Nature Writing: A half-day workshop with Kathryn Aalto
October 23,
1:00 pm – 4:00 pm
Narrative Nature Writing: A half-day workshop with Kathryn Aalto
+ 2 More
events on October 23, 2026
Saturday, October 24
24
, October 2026, 5 events
October 23 – October 28:
Garden Chores & Coffee: Houseplant Care for Fall & Winter
October 24,
11:00 am – 3:00 pm
★
Featured:
The Jazz Perpetrators
October 24,
1:30 pm – 4:30 pm
Eastport Shuffle
October 24,
3:00 pm – 4:00 pm
Celebrating a Literary Treasure: Winnie-the-Pooh at 100
+ 1 More
events on October 24, 2026
5 ongoing events
in the week of October 25
Advantages of Services in AHD Clinic
Creative Circle – Monthly Meetup (2026)
English Dance to delightful live music, excellent callers and friendly community
English Dance to delightful live music, excellent callers and friendly community
First Exposure: Beginner Photography (4- week workshop)
See them in the list
Sunday, October 25
25
, October 2026, 5 events
October 23 – October 28:
★
Featured:
Garden Chores & Coffee: Houseplant Care for Fall & Winter
October 25,
11:00 am – 3:00 pm
★
Featured:
Dan Haas
October 25,
4:00 pm – 7:00 pm
★
Featured:
The Devaney Brothers
October 25,
2:00 pm – 4:00 pm
Paint & Sip
+ 1 More
events on October 25, 2026
Monday, October 26
26
, October 2026, 3 events
October 23 – October 28:
Garden Chores & Coffee: Houseplant Care for Fall & Winter
October 26,
5:30 pm – 8:00 pm
★
Featured:
Mahjong 102 | Guided Play – The Gardens
October 26,
4:00 pm – 7:00 pm
Alliance Material Handling Trunk or Treat
Tuesday, October 27
27
, October 2026, 2 events
October 23 – October 28:
Garden Chores & Coffee: Houseplant Care for Fall & Winter
October 27,
5:30 pm – 8:00 pm
★
Featured:
Mahjong 101 | Beginner Class – The Gardens
Wednesday, October 28
28
, October 2026, 2 events
October 23 – October 28:
Garden Chores & Coffee: Houseplant Care for Fall & Winter
October 28,
10:00 am – 11:00 am
★
Featured:
Holiday Planning & Entertaining
Thursday, October 29
29
, October 2026, 1 event
October 29,
4:00 pm – 7:00 pm
★
Featured:
Joey Fitz
Friday, October 30
30
, October 2026, 3 events
October 30 – November 4:
★
Featured:
Garden Chores & Coffee: Final Steps for Putting Your Garden to Bed
October 30,
4:00 pm – 7:00 pm
★
Featured:
Michael McHenry
October 30,
5:30 pm – 7:30 pm
Folklore & Folktales Exhibit / Closing Reception + Artist Happy Hour
Saturday, October 31
31
, October 2026, 4 events
October 30 – November 4:
Garden Chores & Coffee: Final Steps for Putting Your Garden to Bed
October 31,
4:00 pm – 7:00 pm
★
Featured:
Adam Merkle
October 31,
6:30 pm – 9:30 pm
Contra Dance to delightful live music, excellent callers and friendly community
October 31,
6:30 pm – 9:30 pm
Contra Dance to delightful live music, excellent callers and friendly community
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