| Date | Event | Town | Info |
| 10/7 | Friday Night at the Movies – Beetlejuice | Jamaica Plain |
|
| 10/8 | Screening of Boston's Latino Pioneers / Los Pioneros Latinos de Boston | Jamaica Plain |
|
| 10/8 | Jamaica Plain Fall Fair | Jamaica Plain |
|
| 10/8 & 10/9 | Oktoberfest by Time Our Market Boston | Boston |
|
| 10/13 | Candlelight: A Haunted Evening of Halloween Classics | Brookline |
|
| 10/15 | Cushing Carnival Comes to Newton | Newton |
|
| 10/15 | Walking Tour with Historic Newton | Newton |
|
| 10/16 | Newton Harvest Fair | Newton Centre |
|
| 10/16 | Brookline Dog Day | Brookline |
|
| 10/19 | Red Cross Blood Drive | Newton |
|
| 10/22 | Halloween Extravaganza at the Farmer's Market | South Boston |
|
| 10/28 | Haunted River Run | Boston |
|
| 10/29 | Halloween at Coletti-Magni Park | Newton |
|
| 10/29 | The 15th Annual Halloween Fundraiser | Boston |
|
| 10/29 | Doggone Halloween Dog Parade | Boston |
|
| 10/29 | Halloween Window Painting | Newton |
|
