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Like most areas of the Tri-State area (NYC, NJ, southern Connecticut), New Haven lies at the cross roads between the New England climate to the north and the milder East Coast climate to the south.
Spring ( April to mid May) is mild in New Haven, with high temps in the 50's, 60's, to lower 70's F on average. By late May, summer heat and humidity often arrive as the winds shift to the south. From June through September New Haven is sunny and often hot, with high temps in the 80's F. Coastal areas of New Haven (like Lighthouse Park and beach) see breezy conditions and are often cooler than areas in the centre of the city. Brief summer thunderstorms are common on hot summer days. Fall weather arrives in October, and both October and November are often mild to cool (high temps from 45 to 60 F), though late November can turn blustry and cool (highs only in the 40's F). The winter months (Dec - early March) see cool to cold high temps (30's and 40's F) and a mix of rain and snow. New Haven is fairly sunny in spring, summer, and fall, while the three winter months are the most cloudy.
Most sidewalk cafes are open from April though mid November in New Haven. The warm summers months (late May though September) often see the most events and concerts on the green in New Haven, though there are events throughout the year. Travel between NYC and New Haven (90 minutes each way) is common, and trains leave New Haven every hour for Manhattan. Yale University plays a major role in the life of New Haven, especially in the downtown area. So sidewalks and downtown shops, restaurants, museums and theaters are often the most crowed in fall and spring semesters. The beaches to the east of New Haven along the Connecticut are most popular from late May through early October, as is the cities small beach at Lighthouse Point Park.