By Long Island Sound, along the lower reaches of the Saugatuck River lies one of the richest towns of its size in the United States. Westport has an artistic pedigree and the sort of sophisticated downtown that you would never expect from a town of just 25,000.

1. Downtown Westport


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Downtown Westport

The sort of central business district that any town would aspire to, Downtown Westport blends the cuteness and charm of a New England coastal town with cosmopolitan shopping and dining.

2. Sherwood Island State Park

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Sherwood Island State Park

Purchased in 1914, Sherwood Island is Connecticut’s first state park, and is still considered one of its best.

3. Water Activities

Among the shops and eateries on Riverside Avenue is Downunder Westport, a watersports shop selling surf boards, paddleboards, kayaks and all the gear to go with them.

4. Compo Beach

Compo Beach is a wide, gently curving bay, just where the Saugatuck River flows into Long Island Sound.

5. Earthplace

A natural history museum, nature center and sanctuary rolled into one, Earthplace is an edifying attraction set in more than 60 acres and dating back to 1958.


6. Westport Library

The town’s library has a perfect location, right on the Saugatuck River and when we wrote this article in 2019 had just come through a spectacular transformation project.

7. Westport Country Playhouse


With a national reputation, this professional producing theatre is run on a not-for-profit basis under the artistic direction of the esteemed Mark Lamos.ion for the Performing Arts

Source: Levitt Pavilion For The Performing Arts / facebook

Levitt Pavilion For The Performing Arts

On a scenic little peninsula in the Saugatuck River, the Levitt Pavilion for the Performing Arts hosts one of the biggest and oldest outdoor summer festivals in the United States.

9. Westport Historical Society

Set up way back in 1889, the Westport Historical Society is headquartered at the refined Wheeler House, which dates from 1795 and was updated in an Italianate style in the 19th century.

10. Westport Arts Center

We’ve seen that Westport has a real love for culture, and this multidisciplinary venue was founded some 50 years ago to help keep the local arts scene vital.

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11. Westport Astronomical Society

Over the last half century thousands of people have experienced the wonders of the night sky at this volunteer-run, non-profit observatory.

12. Westport Farmers’ Market

Paul Newman himself opened the Westport Farmers’ Market in 2006. The market grew quickly and soon moved to its current location at 50 Imperial Avenue.

13. Norwalk

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Maritime Aquarium

Westport’s neighbour to the west is a brief drive or just eight minutes in the train, and there are a lot reasons to make the journey.

14. Gallaher Mansion and Cranbury Park

This park is barely ten minutes away in Norwalk and is composed of 227 acres of beautiful parkland and sculpture gardens around the Tudor Revival Gallaher Mansion.

15. Southport Beach

Southport Beach

Not far east of Sherwood Island is another place to unwind in the sun or take a bracing walk on a winter’s day.