Events and Things to Do in Trumbull, CT

Tuesday, October 6

Featured

Any Doctor. Any Hospital that accepts Medicare. Why people love Medicare Supplement Plans!

OCT

6

1:00 PM

Orange, CT

Hate worrying about networks, traveling, or will something be approved? Come see if a Medicare Supplement makes sense for you....

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Wednesday, October 7

Featured

A Slice of History: Connecticut's Pizza Legacy with Author Colin M. Caplan

OCT

7

9:00 AM

Trumbull Library: Main Branch, 33 Quality St, Trumbull, CT

Join Connecticut’s Pizza Guru, Colin M. Caplan, for a fascinating journey through the rich history of local pizza! Caplan will...

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Featured

It’s Fall, Y’all! — Bridgeport Tech Collective Community Mixer + Idea Exchange

OCT

7

5:30 PM

Frenchies Coffee Bar | Bridgeport, 45 E Main St, Bridgeport, CT

Bridgeport’s technology community is growing—and your voice belongs in the room. Join us for a relaxed early-fall evening of...

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Thursday, October 8

Featured

Your Final Application Review Starts Here

OCT

8

7:00 PM

Westport, CT

Join experts Susan M. and Megan B. for a free live webinar designed to give you the competitive edge before early deadlines....

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Sunday, October 11

Featured

Sing for Your Supper

OCT

11

3:00 PM

Easton Library Community Room, 691 Morehouse Rd, Easton, CT

The Easton Arts Council presents a musical tribute featuring the music of Rodgers and Hart performed by the Hot to Trot Trio,...

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Saturday, October 17

Featured

Bingo at Stepney Fire with American Ninja Warrior’s Joe “The Weatherman” Moravsky

OCT

17

5:30 PM

88 Main St, Monroe, CT

Join the Stepney Volunteer Fire Co. No. 1 Inc. for a fun-filled Bingo Night fundraiser on Saturday, October 17, 2026, at...

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Saturday, October 24

Featured

Paper Shredding Event (on-site) with Stratford Rotary - Electronic Collection

OCT

24

9:00 AM

1000 W Broad St, Stratford, CT

Bring your sensitive documents to be shredded on-site. Reasonable pricing and easy drive-thru service. STRATFORD ROTARY WILL BE...

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Featured

Campaigning Class For Next Wave of Women in Politics

OCT

24

10:00 AM

Westport, CT

Future political candidates and campaigners can learn what it takes to win elections Saturday October 24, 10 a.m. to 3 p.m. in...

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Tuesday, November 10

Featured

Greenwich Medical Spa Newtown First Look & Ribbon Cutting

NOV

10

10:30 AM

Newtown, CT

Join Greenwich Medical Spa as we celebrate the opening of our newest location in Newtown with a special First Look & Ribbon...

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Tuesday, October 6

• Any Doctor. Any Hospital that accepts Medicare. Why people love Medicare Supplement Plans! 1:00 pm

  Orange Community Center, 525 Orange Center Rd, Orange

  
  

Wednesday, October 7

• A Slice of History: Connecticut's Pizza Legacy with Author Colin M. Caplan 9:00 am

  Trumbull Library: Main Branch, 33 Quality St, Trumbull

  
  
• It’s Fall, Y’all! — Bridgeport Tech Collective Community Mixer + Idea Exchange 5:30 pm

  Frenchies Coffee Bar | Bridgeport, 45 E Main St, Bridgeport

  
  

Thursday, October 8

• Your Final Application Review Starts Here 7:00 pm

  Online Webinar

  
  

Saturday, October 10

• US Coast Guard Glee Club Concert (7:00pm) and Spaghetti Supper (5:30pm) 5:30 pm

  Nichols United Methodist Church, 35 Shelton Rd, Trumbull

  
  

Sunday, October 11

• Sing for Your Supper 3:00 pm

  Easton Library Community Room, 691 Morehouse Rd, Easton

  
  

Wednesday, October 14

• Statewide Conversation Addressing Compassionate Health Care in the Age of AI 8:00 am

  1073 N Benson Rd, Fairfield

  
  
• Join Weekly Wellness Sessions Through December 16 to Aid Mind, Body & Spirit 6:00 pm

  Trumbull Congregational Church, 3115 Reservoir Ave, Trumbull

  
  
• Free College Admissions & Financial Aid Workshop 6:15 pm

  R.D. Scinto, 1 Corporate Dr, Shelton

  
  

Thursday, October 15

• A new Medicare Advantage option just arrived in Connecticut. 1:00 pm

  Milford Senior Center, 7 Jepson Dr, Milford, CT (only 40 seats)

  
  

Saturday, October 17

• Bingo at Stepney Fire with American Ninja Warrior’s Joe “The Weatherman” Moravsky 5:30 pm

  88 Main St, Monroe

  
  
• Restoring Hope 2026 6:30 am

  Tashua Knolls Golf Club & Banquets, 40 Tashua Knolls Ln, Trumbull

  
  
• OCD Connecticut Walk (Fairfield, CT) 9:00 am

  Jennings Beach, 880 S Benson Rd, Fairfield

  
  
• The Country Store Fair and Tag Sale 9:00 am

  Grace Lutheran Church, 150 Chapel St, Stratford

  
  
• Hat Coat and Sweater Drive 10:00 am

  220 Shelton Rd, Trumbull

  
  

Monday, October 19

• Aetna 2027 plans: the good, the bad, and what to ask. 6:30 pm

  St Ann Church, 501 Naugatuck Ave, Milford

  
  

Wednesday, October 21

• Join Weekly Wellness Sessions Through December 16 to Aid Mind, Body & Spirit 6:00 pm

  Trumbull Congregational Church, 3115 Reservoir Ave, Trumbull

  
  
• Another Medicare enrollment, more confusing plans. Let, Jim guide you. 6:30 pm

  Webinar - Aetna 2027 plans from your couch, live online.

  
  

Thursday, October 22

• The Enchanted Castle Presented by the Junior League of Eastern Fairfield County 4:00 pm

  739 Old Post Rd, Fairfield

  
  
• Time is counting down for you to apply for Medicare plans. 6:30 pm

  Total Mortgage Building's Conference Room - 185 Plains Rd, Milford