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Westport Country Playhouse

Visit Westport: 5 Amazing Things to Do in Westport (2023)

Located by Long Island Sound, just along the lower parts of the mesmerizing Saugatuck River, is the beautiful town of Westport in Connecticut. Westport is one of the richest towns in the United States, having an artistic pedigree that you would expect from a sophisticated downtown. A town of just 25,000 people, Westport is one of the best cities to visit in the magnificent state of Connecticut.

In fact, such is the beauty of this town that actor Paul Newman had moved to Westport in the early 1960s and stayed here until he passed away in 2008. He was an active member of the Westport community and a driving force behind promoting the highly-regarded Westport Country Playhouse. He even gifted land to the city and opened the Farmer’s Market of Westport in 2006.

Visitors are heartily welcome to this postcard-worthy town with its beautiful beaches and quiet streets that are lined with white picket fences and manicured lawns. Watch the serene Saugatuck River make its way through the heart of this city as many wildlife flock to its shores, including turtles, swans, and Ibis.

There are many exciting things to do in Westport. From hitting the excellent public beaches in the town to paddle boarding on the Saugatuck River or catching an outdoor concert at the renowned Levitt Pavilion, there are so many things to do that you will be confused as to what to indulge in first. To help you decide, here are some of the top-rated things to do in Westport.

1. Checking out the Ruth Steinkraus Cohen Bridge

From majestic buildings to iconic bridges, Westport indeed has it all. You will see two rows of waving flags welcoming visitors to Westport’s historic and scenic downtown. Lining the Ruth Steinkraus Cohen Bridge are more than 40 flags that fly all the way from late April right to Thanksgiving. The famous Ruth Steinkraus Cohen Bridge crosses the mesmerizing Saugatuck River and is a beautiful site to take some awe-inspiring pictures.

The bridge is actually a representation of the efforts of the private secretary of Eleanor Roosevelt, by the name of Steinkraus Cohen, who was an avid advocate for the United Nations and went on to found the United Nations Association of Southwest Connecticut. The bridge today represents the huge amount of effort she and other residents of Westport put in to build relationships between towns, people, and countries.

2. Building a sandcastle at the beautiful Compo Beach

Compo Beach is one of the main tourist destinations in Westport. It is also rated as one of the best beaches in Connecticut. This lush area is spread out over 29 acres of park, which is also home to a skating park, basketball courts, marina, pickle ball courts, beach volleyball courts, a pavilion, children’s playground, and a baseball diamond as well.

The soft sandy base of the beach faces the Long Island Sound. You can build a sandcastle, enjoy an ice cream, wander the boardwalk, or just splash around in the calm water of the beach. One of the best times to visit Compo Beach is to catch the sunset, which is best viewed from the western section of the beach, going past the historic cannon kept here.

The beach remains open all year round, but you have to pay $70 on weekends and $45 on weekdays to spend time on this beach if you are not from Westport. The beach also welcomes dogs, but only if they are leashed.

3. Catch a show at the famous Westport Country Playhouse

The Westport Country Playhouse was once home to the late actor Paul Newman and his wife Joanne Woodward for almost 50 years. You will find quite an artsy crowd in Westport, and in fact, there is a lot of talent in the town that every performance is a treat to watch.

The Westport Country Playhouse was transformed into a theater in 1931. During that time, the theater featured acts by many would-be Broadway stars. In 2005, the theater underwent a complete renovation and turned into the state-of-the-art establishment that you can see today. In fact, big stars like Paul Newman, Robert Redford, Jane Fonda, James Earl Jones, and many others have graced the stage here.

Live performances go on from April to November, while at other times of the year, community events, educational programs, and play readings take place at this nationally recognized theater.

4. Get inspired at MOCA Westport

MOCA, or the Museum of Contemporary Art in Westport, is truly an incredible place. Earlier known as the Westport Arts Center, this hugely popular center moved to a new location on the Newtown Turnpike in 2019. The museum has been an integral part of the Westport town for almost 50 years.

MOCA features many artists from all fields, ranging from seasoned professionals to beginners. No matter which type of culture you prefer, be it painting, sculptures, contemporary pieces, films, or chamber music, there is something for everyone to remain entertained.

5. Enjoy the stars at the Westport Observatory

One of the few observatories in Connecticut, the Westport Observatory is the perfect place to get up close to the solar system. Also known as the Rolnick Observatory, the place is home to a large telescope, which is kept inside the dome on top of an old NIKE radar tower. Today, there is a new Celestron EdgeHD telescope to provide the best quality viewing for visitors.

This beautiful observatory sits atop one of the highest spots in the city and is run by volunteer members of the Westport Astronomical Society, which is a non-profit organization. The observatory also runs various events throughout the year, from meteor show viewing to up close viewing of a full moon or solar eclipse.

The observatory remains open to the public on Wednesday evenings from 8 pm to 10 pm. Still, it does depend on the weather and other circumstances. In the summer months, you will find the giant 25-foot Obsession telescope sitting on the lawn of the observatory. This telescope is one of the largest ones in all of Connecticut.

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