Events and Things to Do in Stratford, CT

Wednesday, October 7

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...

Share

Featured

Speaker Spotlight: Ellie Haney

OCT

7

6:00 PM

Harborside Middle School, 175 High St, Milford, CT

Join Ellie Haney, founder of Here For You Clothing, for a meaningful conversation as she shares her personal mental health...

Share

Saturday, October 10

Featured

Pre-Demolition/Moving Sale

OCT

10

9:00 AM

112 Roseville Rd, Westport, CT

Pre-Demolition/Moving Sale There are lots of great items in this house and the parts of the house are for sale. Windows,...

Share

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...

Share

Tuesday, October 13

Featured

Turning 65? Know Your Medicare Options

OCT

13

7:32 PM

Milford Arts Council, the MAC, 40 Railroad Ave, Milford, CT

Medicare doesn't have to be confusing. Attend any of our free information seminars hosted by Trish Pearson Insurance to...

Share

Saturday, October 17

Featured

10th Annual Milford Artisan Market

OCT

17

10:00 AM

168-176 Broad St, Milford, CT

The 10th Annual Milford Artisan Market will take place on Saturday and Sunday, October 17-18, 2026, from 10:00 am to 4:00 pm on...

Share

Sunday, October 18

Featured

Fall Open House - Notre Dame High School

OCT

18

10:00 AM

West Haven, CT

Fall Open House - 10:00amDiscover all that Notre Dame High School has to offer at our Fall Open House. Meet students, faculty,...

Share

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...

Share

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...

Share

Wednesday, October 7

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

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

  
  
• Speaker Spotlight: Ellie Haney 6:00 pm

  Harborside Middle School, 175 High St, Milford

  
  

Saturday, October 10

• Pre-Demolition/Moving Sale 9:00 am

  112 Roseville Rd, Westport

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

  Martin-Bishop Field, 111 Long Hill Rd, Guilford

  
  
• Walk the Walk 1:00 pm

  275 Huntington Rd, Stratford

  
  
• Come Out and Walk the Walk 1:00 pm

  Unitarian Universalist Church of Greater Bridgeport, 275 Huntington Rd, Stratford

  
  

Tuesday, October 13

• Turning 65? Know Your Medicare Options 7:32 pm

  Milford Arts Council, the MAC, 40 Railroad Ave, Milford

  
  

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)

  
  

Saturday, October 17

• 10th Annual Milford Artisan Market 10:00 am

  168-176 Broad St, Milford

  
  
• Restoring Hope 2026 6:30 am

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

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

  Grace Lutheran Church, 150 Chapel St, Stratford

  
  
• Burying Grounds Tours 11:00 am

  Old Congregational Burying Ground, 2203 Main St, Stratford

  
  

Sunday, October 18

• Fall Open House - Notre Dame High School 10:00 am

  Notre Dame High School, 1 Notre Dame Way, West Haven, CT, 06516

  
  
• Traintober 11:00 am

  Boothe Memorial Park, 5800 Main St, Stratford

  
  

Monday, October 19

• Landscape in Oils Demo by Frank Bruckman 11:45 am

  Shelton Community Center, 41 Church St, Shelton, CT

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

  St Ann Church, 501 Naugatuck Ave, Milford

  
  

Tuesday, October 20

• Specters Galore from Forest to Shore Walk 5:00 pm

  Stratford Baldwin Center, 1000 W Broad St, Stratford

  
  

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.

  
  

Thursday, October 22

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

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