Yes

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

Why? Because it's not very warm out.
54°F12°C & Cloudy

Wind is 4 mph7 km/h from the N, gusting to 11 mph17 km/h
May 7
5am54°F12°C5 mph8 km/h NPartly Cloudy
6am52°F11°C5 mph8 km/h NMostly Clear
7am55°F13°C5 mph8 km/h NClear
8am59°F15°C5 mph8 km/h NClear
9am63°F17°C5 mph8 km/h NClear
10am66°F19°C5 mph8 km/h NClear
11am69°F21°C4 mph6 km/h NClear
12pm72°F22°C4 mph6 km/h NClear
1pm74°F23°C4 mph6 km/h NWClear
2pm76°F24°C4 mph7 km/h NWClear
3pm77°F25°C5 mph9 km/h NWMostly Clear
4pm77°F25°C6 mph10 km/h NWMostly Clear
DateLowHighWindDayNight
May 752°F11°C77°F25°C5 mph8 km/h from NWMostly ClearPartly Cloudy
May 849°F9°C63°F17°C6 mph10 km/h from SRainDrizzle
May 948°F9°C70°F21°C6 mph10 km/h from NMostly CloudyRain
May 1045°F7°C52°F11°C8 mph13 km/h from NEDrizzleMostly Cloudy
May 1143°F6°C60°F16°C6 mph9 km/h from NMostly CloudyMostly Cloudy
May 1243°F6°C62°F16°C6 mph9 km/h from SMostly CloudyMostly Cloudy
May 1345°F7°C68°F20°C5 mph8 km/h from WPartly CloudyPartly Cloudy

Yes

Low of 49°F10°C, High of 63°F17°C
Wind: 6 mph10 km/h
Precipitation: 55% rain

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