Fifteen cost-effective yet captivating activities to fall in love with in Westport this summer

For various occasions, lots of people set up full blown picnics along the shores of Compo Beach. Here, one woman tends to the multiple tables she sets up and enjoys with her family.

Photo by Nina Bowens ’25

For various occasions, lots of people set up full blown picnics along the shores of Compo Beach. Here, one woman tends to the multiple tables she sets up and enjoys with her family.

I think everyone can agree that summer is by far the best season of the year. No school, no work and no stress. You get to do anything and everything you want all day long. But what exactly IS there to do? If not occupied with work, camps or summer reading, what are some fun ways to spend your summer in Westport without getting bored? When I run through the typical pool days and binge watching, I often find myself bored. Alas, if you too suffer from the same midsummer slump, fear no longer. I am here to cure just that and provide useful activities that I failed to utilize last summer when I exhausted my usual options. 


Longshore Sailing offers four person catamaran boats in which I often enjoyed last summer with my friend Riley Kosakowski ’25. (Photo by Nina Bowens ’25)

From just $50-75, you and your friends can rent sailboats or catamarans at Longshore Sailing School. My friends and I did this a lot last summer and thoroughly enjoyed the Sound breeze and tanning on the water. The biggest boat seats up to four people, and only one of you needs to know sailing basics to take the boat out for an hour or two. You can travel up and down the entry area to the Saugatuck River, fish or swim out to Kokini Island from one of the sailboats. You can also bring music or a card deck on a less windy day. I found myself easily entertained and tanned by the end of the experience. Additionally, the staff are extremely helpful and reassuring. If you find yourself invested in sailing, feel free to sign up for one of their programs.


This activity is highly recommended, but it might take a couple of days or weeks. Westport has no shortage of ice cream and gelato shops, and most people have their go to’s. However, have you ever truly tried each store in comparison to its competitors? Pick a relatively standard flavor that will be available at all stores, and create a set of criteria specific to your preference. Then, compare each store and rank them based on that rubric. This will leave you with your ultimate Westport ice cream location to value throughout the year, specific to your taste buds. Some great places to check out include Cold Fusion Gelateria, Sunny Daes, Saugatuck Sweets, La Fenice and more chain like stores such as Carvel, Dairy Queen and Baskin Robbins. Take your time with this one. 



Just 20 minutes from downtown Westport, by Calf Pasture Beach, there’s a hidden entertainment gem which costs just $9 per player. Cove Marina Mini Golf allows you to pick your favorite color ball, club and begin playing an enjoyable round of 18 holes. Right next door is the delicious Sunset Grill which serves seafood right by the boat dock. The mini golf course features many ocean-themed obstacles like anchors or buoys, and is extremely entertaining for a low cost. To learn more, call 203-853-8282.


My own friends and family enjoyed a smaller scale picnic last summer in which we brought cushions and yummy food for my dad’s birthday. I found it rather enjoyable. (Photo by Nina Bowens ’25)

Many enjoy the wonders and attributes that Compo Beach has to offer, such as the playground, Hook’d or the skate park. However, if you are tired of coming midday and swimming around, try setting up a nice beach picnic to watch the sunset. The best side of the beach to watch from is the southwest side facing Kokini Island. The picnic can be formal, with cushions and tables, or informal, with simple beach chairs and good music. Either way, bring good food! You can buy dinner at Hook’d, the beach restaurant, or bring some from home. A good card game or good company will make this activity quickly join your usual schedule.


The Remarkable drive-in Theater served as a major entertainment spot last summer, and will continue to do so this upcoming season. Pictured here, the theater displayed “The Sandlot” to various viewers in early August, 2022. (Photo by Nina Bowens ’25)

Covid-19 brought a lot of hardship not only in Westport, but around the world. One small silver lining of the pandemic, however, was the gift of Remarkable Theater launching during that time stretch. It was so successful that it continues to entertain Westporters even after the pandemic is over. The drive-in theater is a blast to the past, and allows you to turn off your car but keep your radio on and enjoy a varied array of movies changing weekly. Last summer I went to watch “The Sandlot ” with my sisters, and I found it much more enjoyable than the actual cinema due to the ambiance. The theater is located in the lot of 50 Imperial Avenue. To find out more visit their online website.




The Westport Farmers Market’s summer season is officially open. They set up stands every Thursday from 10 a.m.- 2 p.m. at 50 Imperial Avenue. They have 14 local vendors ranging from pizza dough companies to seasonings to sandwich shops. They also tend to have entertainment for kids, such as tiki tents or face painting. The Market is right by the Saugatuck River, so enjoying fresh food on the Library Riverwalk is definitely a must this summer. 



The Westport Astronomical Society is the perfect spot for someone who enjoys stargazing, such as myself. I only recently found out about the location, which is 182 Bayberry Lane. They are a non-profit group that works to provide solar experiences for free every Wednesday night from 8-10 p.m. if the skies are clear. On other days, the cost is $5 admission per person. Not only are you allowed to come view the stars, but also learn about them as the observatory provides a bridge between amateur viewing and professional research through their memberships and classes. Visit this site to learn more.

Alas, if you too suffer from the same midsummer slump, fear no longer. I am here to cure just that and provide useful activities that I failed to utilize last summer when I exhausted my usual options.

— Nina Bowens ’25



The Levitt Pavilion offers free concerts for the citizens of Westport in their open auditorium right behind the Westport Library. Throughout the summer they are expected to have various artists and bands perform including Grammy winning Jazz Artist Samara Joy on June 3. Not only does the Levitt provide free music, but sometimes stand up comedians come to entertain. It is a free activity to attend in a beach chair or towel, with friends or family. Keep updated with the schedule here to see what is upcoming.


Many highschoolers utilize Compo’s public basketball courts to hoop with their friends. This is one of the many spots that Westport has to offer in regards to public lifetime sports. (Photo by Nina Bowens ’25)

Westport offers so many free public spaces that can allow you to learn various skills or lifetime sports. If you are feeling bored, go learn one! For example, Compo Beach offers basketball courts, skateboard parks, pickleball courts, a baseball diamond and a large lawn to learn beach games such as spikeball or practice ProKadima. These spaces can benefit you should you find yourself with excessive amounts of free time and lack ideas. Bring another amateur friend and challenge them to a pickleball tournament!


Here are some of my top Trader Joe’s snacks, with the famous “Gone Bananas” featured at the top. They offer many more frozen or sweet treats. (Photo by Nina Bowens ’25)

Everybody knows that the best unique snacks a grocery store can offer are all found at Trader Joe’s. They offer their own individualized versions of classic snacks, but in every case, they end up tasting better! For example, instead of Oreo’s, go to Trader Joe’s and buy their “Joe Joe’s,” marketed by their famous pecan bird. Or, my personal favorite, try their “Gone Bananas!” snack which features a white box with a monkey on it, full of frozen banana slices covered in chocolate. These are just two of the various delectables found within the store. One of my favorite activities last summer was trying as many snacks as I could and deciding which would be my forever go-to.



Similarly to Longshore, Sea Kayak Rentals right by Saugatuck Sweets offers various forms of water activities and transportation. The standard paddleboard, canoe and kayak are available, but they also have more modern devices such as the step-board. Last summer I rented a step-board with my sister and mom and found it way more fun than regular paddleboarding. Essentially, you stand up and walk on these step pads, almost like a bike and scooter combination, and propellers under the water navigate you throughout the river. The rentals range depending on how long and which activity you choose to do, and this is definitely on the more expensive side of activities listed, but it is super refreshing and enjoyable, especially on a hot summer day. To find out more, call 203-557-6033.


This board welcomes all visitors to the Caryl & Edna Nature Preserve, telling their story and explaining the layout of the park. (Photo by Nina Bowens ’25)

A quieter alternative to Winslow Park is the Caryl & Edna Haskins Preserve off of Green Acre Lane. The walk takes all of 30 minutes or less, and is filled with local wildlife such as toads, turtles, deers and more. The walk begins with a board describing the Haskins’ lives and their contributions to the town of Westport, which is quite intriguing.They also have various picnic tables where one might enjoy lunch or a book. The quiet atmosphere surrounded by nature serves as the perfect break from one’s day to day life.



Another option for tanning or nature walks is the Sherwood Island State Park. Located Just of the Long Island Connector, the park itself is huge and offers a long shoreline and a 10-15 minute nature walk throughout its various 238 acres of beach, wetlands and woodlands. It additionally offers food concessions, or you can visit the Connecticut 9/11 memorial that is located within the park. 


The Westport Country Playhouse stands welcoming visitors with its greenery and outside picnic tables. Various shows will be performed here throughout the summer months. (Photo by Nina Bowens ’25)

The Westport Country Playhouse offers various shows throughout the year and the summertime, providing a perfect local entertainment location. Unlike the Levitt Pavilion, most shows at the Playhouse require purchased tickets that can vary in range. The building offers concessions, outside picnic tables and of course the lovely theater. This summer various groups are performing “The Magic School Bus,” “Quick Service,” “Below Surface,” Agatha Christie’s “The Murder of Roger Ackroyd” and more. Check out the show dates here.


Westport is a town full of festivals, fairs and opportunities, especially throughout the summer season. Downtown offers a variety of options such as the Summer Music Festival from July 10-21 by Greens Farms Academy, or the Westport Downtown Association’s Music on Church Lane continuous event that books various artists to play live every Friday and Saturday night. Later on in the summer Saugatuck celebrates their annual Slice of Saugatuck festival on Sept. 10 which celebrates local food vendors. All of these events are open to the public for little or no money and are filled with locals supporting locals.