By Jamie Santarella
Just about 52 miles northeast of New York City, Westport sits on Long Island Sound within Connecticut's Gold Coast.
It's not quite small, and it's not too big, with about a population of 28,000. There isn't much to do besides going to the beach, perusing the shops downtown, or lunching at your favorite spots, so the convenience of NYC is nice.
Some people love Westport, some people hate it. Generations of my family have grown up here and then stayed, and if it wasn't Westport, it was a town over. With most of my family extended only a 10 to 20 minute drive from me, and its New England beauty during any season, I love it.
Compo Beach
JAMIE SANTARELLA / UP Blog Writer
The beach is probably the busiest place in town all year round (yes, even in the winter there are people there running, walking, playing with their dogs). It definitely attracts the most out-of-town or out-of-state visitors during the warmer months, and it provides a nice, scenic drive that I never get tired of.
Main Street
JAMIE SANTARELLA / UP Blog Writer
Main Street, or "downtown," is where all the shopping is. From bigger chains like Anthropologie, J. crew, and Urban Outfitters to smaller businesses, it has quite a lot of places to shop, and of course, to eat.
Saugatuck
JAMIE SANTARELLA / UP Blog Writer
Saugatuck is a neighborhood in Westport that has more restaurants and shops, but also one of my favorite parts of town. During the holidays, the Cribari Bridge over the Saugatuck River is lit with Christmas lights. It's a tradition that's cute and festive, and makes for a really fun and pretty drive over the bridge at night.
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