Yes

you do need a jacket based on the weather in Ware, MA 01082, USA 1 second ago

Why? Because it's cool. Pleasantly cool, but cool and it's so windy, your hat is now someone else's problem, two cities away!
57°F14°C & Cloudy

Wind is 9 mph15 km/h from the West, gusting to 27 mph43 km/h
May 18
9pm56°F13°C10 mph16 km/h WestMostly Cloudy
10pm55°F13°C10 mph16 km/h WestMostly Cloudy
11pm54°F12°C11 mph18 km/h NorthwestPartly Cloudy
May 19
12am53°F12°C10 mph17 km/h NorthwestPartly Cloudy
1am52°F11°C10 mph16 km/h NorthwestPartly Cloudy
2am51°F10°C10 mph16 km/h NorthwestPartly Cloudy
3am51°F10°C11 mph18 km/h NorthwestPartly Cloudy
4am50°F10°C11 mph18 km/h NorthwestMostly Cloudy
5am49°F10°C11 mph18 km/h NorthwestMostly Cloudy
6am49°F10°C12 mph19 km/h NorthwestMostly Cloudy
7am50°F10°C12 mph20 km/h NorthwestPartly Cloudy
8am52°F11°C14 mph22 km/h NorthwestPartly Cloudy
DateLowHighWindDayNight
May 1853°F12°C62°F17°C6 mph9 km/h from WestMostly CloudyMostly Cloudy
May 1948°F9°C61°F16°C13 mph20 km/h from NorthwestMostly CloudyPartly Cloudy
May 2045°F7°C59°F15°C7 mph12 km/h from NorthMostly CloudyCloudy
May 2146°F8°C54°F12°C8 mph14 km/h from EastDrizzleRain
May 2244°F7°C49°F9°C13 mph21 km/h from NortheastRainDrizzle
May 2343°F6°C56°F14°C6 mph9 km/h from NorthwestMostly CloudyMostly Cloudy
May 2446°F8°C59°F15°C7 mph11 km/h from NorthwestMostly CloudyMostly Clear

Yes

Low of 48°F9°C, High of 61°F16°C
Wind: 13 mph20 km/h
Precipitation: None

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