Yes

you do need a jacket based on the weather in Bolton, MA, USA 1 second ago

Why? Because looks like it's raining and it's cold enough that makes you wish you had a hat, but you're still too proud to admit it and it's fairly windy outside!
46°F8°C & Rain

Wind is 10 mph16 km/h from the East, gusting to 24 mph39 km/h
May 22
9am46°F8°C10 mph17 km/h EastRain
10am46°F8°C11 mph17 km/h EastRain
11am46°F8°C11 mph18 km/h EastRain
12pm46°F8°C11 mph18 km/h EastRain
1pm47°F8°C11 mph18 km/h EastRain
2pm47°F8°C11 mph18 km/h EastRain
3pm47°F8°C12 mph19 km/h NortheastRain
4pm46°F8°C12 mph19 km/h NortheastRain
5pm46°F8°C12 mph19 km/h NortheastRain
6pm45°F7°C12 mph19 km/h NortheastRain
7pm45°F7°C13 mph20 km/h NortheastRain
8pm44°F7°C14 mph22 km/h NortheastRain
DateLowHighWindDayNight
May 2243°F6°C47°F8°C11 mph18 km/h from EastRainRain
May 2342°F6°C54°F12°C6 mph10 km/h from NorthwestDrizzleDrizzle
May 2446°F8°C56°F13°C8 mph13 km/h from WestCloudyMostly Cloudy
May 2546°F8°C60°F15°C8 mph14 km/h from NorthwestMostly CloudyPartly Cloudy
May 2645°F7°C66°F19°C4 mph7 km/h from NorthPartly CloudyClear
May 2747°F8°C71°F22°C3 mph5 km/h from SouthwestMostly CloudyMostly Cloudy
May 2854°F12°C69°F20°C6 mph9 km/h from SoutheastCloudyDrizzle

Yes

Low of 42°F6°C, High of 55°F13°C
Wind: 6 mph10 km/h
Precipitation: 63% rain

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