October Events and Things to do in Gloucester, MA

Harvard Square Chocolate Tour
Fri, Oct 2, 3:00 PM + 17 more
Cambridge · Harvard Square
Harvard Square Chocolate Tour
Fri, Oct 2, 3:00 PM + 17 more
Cambridge · Harvard Square
Comedy at Summer Shack ($15 + Free Parking!) - Cambridge, MA
Sat, Oct 3, 7:30 PM + 4 more
Cambridge · Summer Shack
Comedy at Summer Shack ($15 + Free Parking!) - Cambridge, MA
Sat, Oct 3, 7:30 PM + 4 more
Cambridge · Summer Shack
The Strayaways: Kevin Burke, Dylan Foley & Eamon O’Leary
Fri, Oct 23, 7:30 PM
Kittery · The Dance Hall
The Strayaways: Kevin Burke, Dylan Foley & Eamon O’Leary
Fri, Oct 23, 7:30 PM
Kittery · The Dance Hall
Just added
BOSTON RETAIL SHOW 2026
Sat, Oct 31, 10:00 AM
Boston · Hynes Convention Center
Just added
BOSTON RETAIL SHOW 2026
Sat, Oct 31, 10:00 AM
Boston · Hynes Convention Center
PMP Exam Prep Bootcamp in Cambridge, MA | 35 Contact Hours PMP Training
Tue, Oct 6, 9:00 AM + 3 more
Cambridge · Regus - Cambridge - Harvard Square Mifflin Place
PMP Exam Prep Bootcamp in Cambridge, MA | 35 Contact Hours PMP Training
Tue, Oct 6, 9:00 AM + 3 more
Cambridge · Regus - Cambridge - Harvard Square Mifflin Place
PMP Certification Bootcamp in Cambridge, MA | Pass the PMP Exam in 4 Days
Sat, Oct 3, 9:00 AM + 8 more
Cambridge · Regus - Cambridge - Harvard Square Mifflin Place
PMP Certification Bootcamp in Cambridge, MA | Pass the PMP Exam in 4 Days
Sat, Oct 3, 9:00 AM + 8 more
Cambridge · Regus - Cambridge - Harvard Square Mifflin Place
PMP Bootcamp in Cambridge, MA | Fast-Track Your PMP Certification in 4 Days
Sat, Oct 3, 9:00 AM + 8 more
Cambridge · Regus - Cambridge - Harvard Square Mifflin Place
PMP Bootcamp in Cambridge, MA | Fast-Track Your PMP Certification in 4 Days
Sat, Oct 3, 9:00 AM + 8 more
Cambridge · Regus - Cambridge - Harvard Square Mifflin Place
Best PMP Certification Training in Cambridge, MA | 4-Day Bootcamp Course
Sat, Oct 3, 9:00 AM + 8 more
Cambridge · Regus - Cambridge - Harvard Square Mifflin Place
Best PMP Certification Training in Cambridge, MA | 4-Day Bootcamp Course
Sat, Oct 3, 9:00 AM + 8 more
Cambridge · Regus - Cambridge - Harvard Square Mifflin Place
Comedy at Bill's Bar ($12) - Boston, MA
Sat, Oct 10, 7:00 PM
Boston · Bill's Bar
Comedy at Bill's Bar ($12) - Boston, MA
Sat, Oct 10, 7:00 PM
Boston · Bill's Bar
OLIVERS AT NIGHT
Sat, Oct 3, 9:30 PM + 4 more
Boston · Oliver's Night Club
OLIVERS AT NIGHT
Sat, Oct 3, 9:30 PM + 4 more
Boston · Oliver's Night Club
Quality Management 1-Day Workshop | Lowell, MA
Thu, Oct 8, 9:00 AM
Lowell · For venue details reach us at info@learnerring.com
Quality Management 1-Day Workshop | Lowell, MA
Thu, Oct 8, 9:00 AM
Lowell · For venue details reach us at info@learnerring.com
Intro to MIG Welding
Sun, Oct 25, 1:00 PM
Portsmouth · Port City Makerspace
Intro to MIG Welding
Sun, Oct 25, 1:00 PM
Portsmouth · Port City Makerspace
Taste of Boston Sampler
Sat, Oct 3, 3:00 PM + 14 more
Boston · Boston Harbor Distillery
Taste of Boston Sampler
Sat, Oct 3, 3:00 PM + 14 more
Boston · Boston Harbor Distillery
VIP Whiskey Tour and Tasting
Sat, Oct 3, 3:30 PM + 9 more
Boston · Boston Harbor Distillery
VIP Whiskey Tour and Tasting
Sat, Oct 3, 3:30 PM + 9 more
Boston · Boston Harbor Distillery
Comedy at Warp and Weft
Sun, Oct 18, 7:00 PM
Lowell · Warp and Weft
Comedy at Warp and Weft
Sun, Oct 18, 7:00 PM
Lowell · Warp and Weft
*Free Sewcial Club!
Wed, Oct 14, 7:00 PM
Boston · Artisan's Asylum
*Free Sewcial Club!
Wed, Oct 14, 7:00 PM
Boston · Artisan's Asylum
*Free Circuit Hacking Night!
Wed, Oct 7, 6:00 PM + 3 more
Boston · Artisan's Asylum
*Free Circuit Hacking Night!
Wed, Oct 7, 6:00 PM + 3 more
Boston · Artisan's Asylum
Precision Edge: The Art of Handplane Sharpening
Thu, Oct 8, 6:00 PM
Boston · Artisan's Asylum
Precision Edge: The Art of Handplane Sharpening
Thu, Oct 8, 6:00 PM
Boston · Artisan's Asylum
Table 4 Tonight: Portsmouth, NH | Dinner with New Friends small town
Thu, Oct 22, 7:00 PM
Portsmouth · Restaurant of the Week
Table 4 Tonight: Portsmouth, NH | Dinner with New Friends small town
Thu, Oct 22, 7:00 PM
Portsmouth · Restaurant of the Week

Trends in Gloucester

Explore more trends

Harvard Square Chocolate Tour

Harvard Square Chocolate Tour

Comedy at Summer Shack ($15 + Free Parking!) - Cambridge, MA

Comedy at Summer Shack ($15 + Free Parking!) - Cambridge, MA

The Strayaways: Kevin Burke, Dylan Foley & Eamon O’Leary

The Strayaways: Kevin Burke, Dylan Foley & Eamon O’Leary

BOSTON RETAIL SHOW 2026

BOSTON RETAIL SHOW 2026

PMP Exam Prep Bootcamp in Cambridge, MA | 35 Contact Hours PMP Training

PMP Exam Prep Bootcamp in Cambridge, MA | 35 Contact Hours PMP Training

PMP Certification Bootcamp in Cambridge, MA | Pass the PMP Exam in 4 Days

PMP Certification Bootcamp in Cambridge, MA | Pass the PMP Exam in 4 Days

PMP Bootcamp in Cambridge, MA | Fast-Track Your PMP Certification in 4 Days

PMP Bootcamp in Cambridge, MA | Fast-Track Your PMP Certification in 4 Days

Best PMP Certification Training in Cambridge, MA | 4-Day Bootcamp Course

Best PMP Certification Training in Cambridge, MA | 4-Day Bootcamp Course

Comedy at Bill's Bar ($12) - Boston, MA

Comedy at Bill's Bar ($12) - Boston, MA

OLIVERS AT NIGHT

OLIVERS AT NIGHT

Quality Management 1-Day Workshop | Lowell, MA

Quality Management 1-Day Workshop | Lowell, MA

Intro to MIG Welding

Intro to MIG Welding

Taste of Boston Sampler

Taste of Boston Sampler

VIP Whiskey Tour and Tasting

VIP Whiskey Tour and Tasting

Comedy at Warp and Weft

Comedy at Warp and Weft

*Free Sewcial Club!

*Free Sewcial Club!

*Free Circuit Hacking Night!

*Free Circuit Hacking Night!

Precision Edge: The Art of Handplane Sharpening

Precision Edge: The Art of Handplane Sharpening

Table 4 Tonight: Portsmouth, NH | Dinner with New Friends small town

Table 4 Tonight: Portsmouth, NH | Dinner with New Friends small town

Things to do around Gloucester

Trends in Gloucester

1. Mothers day

2. Memorial day weekend events

3. Singles events

4. North shore happenings

5. Comedy

6. Kids events today

7. Live music

8. Speed dating

9. Fantasy ball

10. Stage fort park

11. May events

12. Beauport hotel gloucester