Events and Things to Do in Derby, CT

Tuesday, October 6

Featured

The 6th Annual PowHERful Conversations: The Power of Reinvention

OCT

6

8:00 AM

Courtyard by Marriott Shelton, 780 Bridgeport Ave, Shelton, CT

Support women-owned businesses!!! The 6th Annual PowHERful Conversations: The Power of Reinvention, presented by the Women in...

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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

Complimentary Presentation - Preparing for Taxes in Retirement

OCT

7

12:30 PM

Shelton-Derby, CT

During this presentation we’ll discuss three important areas of tax planning for retirement. We’ll look at possible sources of...

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Saturday, October 10

Featured

Miles For Moriah 5K Walk

OCT

10

11:00 AM

Riva, 183 Beach St, West Haven, CT

Join us for a meaningful 5K walk starting and ending at Riva to benefit Moriah's Stockings, a local foundation providing...

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Featured

Oktoberfest: A Fundraiser for Guilford VFW Post 7666

OCT

10

12:00 PM

Martin-Bishop Field, 111 Long Hill Rd, Guilford, CT

Been to an Oktoberfest already this year? There's always room for one more! Saturday, October 10 · 12–7 PM · Martin-Bishop...

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Tuesday, October 6

• The 6th Annual PowHERful Conversations: The Power of Reinvention 8:00 am

  Courtyard by Marriott Shelton, 780 Bridgeport Ave, Shelton

  
  
• 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

• Complimentary Presentation - Preparing for Taxes in Retirement 12:30 pm

  Online Event

  
  

Saturday, October 10

• Miles For Moriah 5K Walk 11:00 am

  Riva, 183 Beach St, West Haven

  
  
• Oktoberfest: A Fundraiser for Guilford VFW Post 7666 12:00 pm

  Martin-Bishop Field, 111 Long Hill Rd, Guilford

  
  

Monday, October 12

• Derby City Hall Closed for State/Federal Holiday - No Delay in Trash/Recycling Pick up this week. Transfer Station open today

  City of Derby Events, Derby

  
  
• WIOA Pathways

  9:30 am

  Southwest Connecticut Job Center – Derby Office, 30 Elizabeth Street, Derby

  
  
• WIOA Pathways (In-Person - Derby)

  9:30 am

  Southwest Connecticut Job Center – Derby Office, 30 Elizabeth Street, Derby

  
  

Wednesday, October 14

• 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)

  
  
• Paranormal Dinner and Ghost Tour - Thursday October 15, 2026

  6:00 pm

  285 Main Street, Derby

  
  
• Paranormal Dinner and Ghost Tour

  6:00 pm

  Twisted Vine Restaurant, 285 Main Street, Derby

  
  

Saturday, October 17

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

  Grace Lutheran Church, 150 Chapel St, Stratford

  
  

Sunday, October 18

• The Art Of The Draw Animation Film Festival 1:00 pm

  10Selden, 10 Selden St, Woodbridge

  
  

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

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

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

  
  

Friday, October 23

• Xtreme Comedy at The Twisted Vine Restaurant

  8:00 pm

  285 Main Street, Derby

  
  

Saturday, October 24

• Derby, CT- The Golden Ghouls- Twisted Vine

  12:00 pm

  Twisted Vine Restaurant, 285 Main Street, Derby

  
  
• Smoke in the Valley Craft Beer and Home Brew Festival

  1:00 pm

  BADSONS Beer Co., 251 Roosevelt Drive, Derby

  
  

Thursday, October 29

• Is it better to get a Medicare Supplement or a Medicare Advantage? 6:30 pm

  St. Ann's Church Parish Hall, 501 Naugatuck Ave, Milford

  
  

Tuesday, November 3

• Could a Medicare Supplement be your best choice? Come find out. 6:30 pm

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

  
  

Sunday, November 8

• PYC Auxiliary Annual Fall Festival 11:00 am

  Pequonnock Yacht Club, 98 S Water St, New Haven

  
  

Monday, November 16

• A new Medicare plan option has landed in Connecticut. Four ways to learn more. 6:00 pm

  Milford Senior Citizen Center, 9 Jepson Dr, Milford

  
  

Sunday, November 22

• Cheshire High School Train Show 10:00 pm

  Cheshire High School, 525 S Main St, Cheshire