My End Of The Summer Trip To The Connecticut Shoreline

Vacation at the Connecticut shoreline

My End Of The Summer Trip To The Connecticut Shoreline

I couldn’t have asked for a better end to the summer. Billy and I took our much anticipated trip to the East Coast. We spent a week and a half in Massachusetts prior to our 10 day vacation in Westbrook, Connecticut (the same seaside town I grew up going to every year). While we were in CT, my parents and I took a day trip to Block Island and explored the picturesque seaside town.

Vacation at the Connecticut shoreline

This past week, I’ve been looking at my photos and reliving the memories of this amazing vacation that I documented on my InstaStories. From the moment I left this quaint beach town, I started missing it and as time goes by I’m missing it even more. I can’t wait to go back next year, but until then I have some beautiful memories to look back on. Here’s everything we did on our trip to the Connecticut shoreline and here's everything I wore.

The Cottage

Cottage at the Connecticut shoreline

My parents, Billy, and I arrived on a sunlit Saturday afternoon, and my sister and her boyfriend came the following morning. My mom found us a charming colonial waterfront cottage that was built in 1890 and it was on the same road as the place we grew up vacationing in. I loved being in a place with so much history, and as a joke I purchased an EMF meter (to detect ghosts) which kept going off in the cellar. There’s a rumor that The Talcott House, (a few houses down from where we stayed), has seen its fair share of supernatural occurrences.

The cottages stone fireplace
Cottage bedroom at the Connecticut shoreline

I saw an interesting picture my sister posted on her Instagram which showcased some beautiful works of art and I asked her where it was from. She had discovered an art studio in the upstairs loft of the garage that was filled with paintings, sketches, and flyers. I ventured up there (I didn’t stay for long because I have an extreme fear of spiders and this looked like a place where they would be), but I was able to snap a few photos. In the master bedroom my dad exposed a hidden closet with more artwork and a crate of vintage records. This is what I love about old homes, the possibility of discovering random treasures.

Art
Art

Mornings At The Shore

I think everyone’s favorite aspect of the cottage was the spacious porch with stunning views of Long Island Sound. I looked forward to waking up fairly early to blog on the porch before I began my day. I also enjoyed reading Bringing Out The Dead (which was on my list of beach must-haves), as I watched the ocean glisten in the sunlight. Each morning the tourists and the locals would go on their morning walks and they would say hello or wave as they passed by—this reinstated the friendly small-town feel of this seaside community.

Cottage on the Connecticut shoreline

Each morning, my family took a short walk down the street and purchased coffee and donuts to bring back to the cottage. When the tide was low Billy and I walked across the street and took a stroll on the sandbars to hunt for seashells.

Westbrook, CT
Collecting seashells at the Connecticut shoreline
A morning beach walk during low tide

Beach Days

The weather was ideal, which called for many days spent on the beach. During the beginning of our trip we took advantage of the low tide by walking far out onto the sandbars and continuing our search for seashells.

Seashell photography

Later on in the week the tide switched with high tide taking place in the afternoon. Growing up, one of my favorite things about spending time at the Connecticut Shoreline was relaxing on the giant “Fun Island” raft as the waves rocked back and forth. We pushed it out to sea and tied it to a buoy spending hours in the ocean. I searched endlessly for something similar but didn’t have any luck so I settled on a pink flamingo float. We all took turns floating on the raft and unwinding in the warm saltwater.

Seaside Ave, Westbrook CT
Beach style
Waves at the Connecticut shoreline
Pink flamingo float in Long Island Sound

I was looking for an alcoholic beverage (preferably a canned cocktail) to sip on while I was laying out on the beach. At the start of the summer, photos of Fishers Island Lemonade started popping up in my newsfeed and when I asked friends back East about it, they told me it tasted incredible. I attempted to purchase it for the Fourth of July here in L.A. but discovered that it’s only available on the East Coast. As soon as I arrived in Westbrook, I stopped at a local package store and picked up this quintessential New England mixed-drink. Each can holds double the volume of alcohol than an ordinary beer and the spiked lemonade is blended with Vodka and Whisky. I wish this delectable concoction was sold on the West Coast.

Fishers Island Lemonade

Evening Adventures

We spent plenty of our evenings exploring the Connecticut shoreline, eating out, shopping and seeing the coastal sights, but there was also a number of nights we stayed in. We watched the sunset on the horizon and went for walks down Seaside Avenue ending up at Pilots Point Marina. As we walked down the street, I was able to share my childhood and teenage memories with Billy, by highlighting the various places I hung out, and the old cottage I stayed in.

A view of the Connecticut shoreline
Sunset at the Connecticut shoreline

We happened to be vacationing during the Labor Day weekend so I brought a box of sparklers I had purchased years ago and used them to celebrate the closing of the summer. We lit them on the beach as our neighbors set off fireworks. It was such a fun and laid back end to an unforgettable vacation.

Sparklers at the beach

The Log Cabin

The Log Cabin in Clinton, CT

After my sister and Hunter arrived on Sunday, the six of us went out to dinner at The Log Cabin in Clinton. This Italian eatery is a place my family has been dining at since the 1980s and it’s not a trip to the shore without at least one visit there. Not only is the food delicious but the portions are enormous. Before our entrées arrived, the table was given bread, salad, and two huge bowls of penne pasta cooked in a savory marinara sauce. We were so full that we ended up taking most of the food back to the cottage to have for lunch the next day.

Water's Edge Resort & Spa

Water's Edge Beach Resort & Spa

My aunt Paula drove down to visit for a couple of days. On her first night there we headed to Water’s Edge Resort and Spa and had dinner at the Seaview Bistro. Water’s Edge is one of my favorite hotels that brings back a ton of nostalgia. We used to spend a week or two in one of their ocean view villas. The memories came flooding back and I was thrilled to show Billy around and point out my most-loved aspects of this waterfront resort.

Dinner at Water's Edge in Westbrook, CT

A Birthday Celebration

Because my aunt and my sister's boyfriend had to leave, we celebrated my dad’s birthday a day early by surprising him with a party. My sister and Hunter picked up a tasty vanilla lemon buttercream cake and I requested Talenti’s Black Raspberry Vanilla Parfait which paired perfectly with it. We spent the evening gathering on the porch and had a wonderful time reminiscing.

Birthday party on the Connecticut Shoreline
Birthday party on the Connecticut Shoreline
Birthday party on the Connecticut Shoreline

Later on we crossed the street to fly a kite that my sister purchased in Olde Mistick Village. Afterwards, we gathered for a family photo on the beach to take advantage of us all being together at our favorite place.

Family photo on the Connecticut Shoreline
The Connecticut Shoreline

Date Night At The Madison

Beach Hotel

When Billy and I were searching for a trendy, upscale restaurant to dine at for a date night, I came across The Wharf at The Madison Beach Hotel. This was my first time visiting this beachside resort that sits on top of a dead-end street and overlooks the Connecticut Shoreline. Immediately upon pulling up, it reminded me of Shutters on the Beach in Santa Monica. 

The Madison Beach Hotel on the Connecticut Shoreline

Before we entered we wandered around the waterfront and it surprised me to discover tide pools in Connecticut. After I raved about our dinner (and the resort), my parents spent an afternoon there.

Tide pools on the Connecticut shoreline

For our appetizer, Billy and I split the queso dip off the bar bites menu which was mouth-watering and perhaps the best queso I’ve ever had. For dinner I looked for the healthiest non-meat entrée I could find and decided on the Mezze Plate; a dish of black bean hummus, corn pico de gallo, cotija cheese, and pickled fresh peppers. To top it off, I had a glass of Pinot Grigio. For Billy’s entrée, he had the Beet & Goat Cheese Gocce; a pasta mixed with Riesling Beurre Blanc, lemon, and sun-dried tomato gremolata.

Beet & Goat Cheese Gocce from The Wharf Restaurant at The Madison Beach Hotel

Once we were finished eating we sat outside on the beach and watched the sunset while live music played in the background. It was such an enjoyable and unforgettable evening.

Saybrook Point 

One evening we ventured over to the Saybrook Point Marina in Old Saybrook. This was a favorite place of mine growing up; my family and I would spend hours playing miniature golf and having dinner at Dock n Dine (which sadly closed because of Hurricane Sandy). After walking around and viewing the boats on the river we stopped at Fresh Salt, a restaurant that’s apart of the Saybrook Point Inn and Spa. We grabbed a table outside which offered unparalleled views of the Connecticut River and the marina.

Saybrook Point Marina at the Connecticut Shoreline
Saybrook Point Marina at the Connecticut Shoreline

I was full from lunch so I ordered dessert and choose an exquisite brownie sundae smothered in ice cream, chocolate, and caramel sauce. Later on in the evening we observed a stunning sunset overlooking the water.

Brownie Sundae from Salt at The Saybrook Point Hotel
Sunset at Saybrook Point Marina

A Day Trip To Block Island

I vaguely recall traveling to Block Island via a family friend's boat when I was about seven years old. Of course, I don’t remember all the details, just that it was such a fun overnight trip. While planning our vacation to the Connecticut shoreline, I came up with an idea to take a boat trip. I narrowed it down to The Hamptons or Block Island and ended up choosing Block Island. After my last vacation to The Hamptons I realized it was too big of a destination to explore in one day.

After driving about 35 minutes to New London, CT, we purchased tickets for the 11AM ferry on the Block Island Express, and for the 6:30PM ferry to head back. The journey took a little over an hour and offered awe-inspiring views as we cruised through Long Island Sound and crossed through Block Island Sound and the Atlantic Ocean.

The Block Island Express

As we pulled up to the harbor, I recognized the view from an episode of The Affair. In the first season Noah and Alison take a ferry boat from Montauk, New York to Block Island so they could pursue their relationship on an island where no one knew them.

A view of Block Island from the ferry

We devoted the day to shopping, dining, sightseeing and walking along the beach. Some of my favorite moments where getting ice cream at The Ice Cream Place, and picking up souvenirs in the little boutiques.

The Ice Cream Place in Block Island

There were tons of fascinating shops that we stopped in, many with authentic handcrafted items. My favorites were The Tipsy Mermaid, Blocks of Fudge, Diamondblue Surf Shop, Blvk Market, and Wild Flowers Boutique where I picked up a beautiful seashell bracelet. Seeing all the handmade crafts inspired me to start making jewelry again.

Tassel necklaces in Block Island
Wild Flowers Boutique in Block Island
Candy shop in Block Island
East of The Nile Trading Company

In between shopping and before dinner I tried a Del’s Frozen Lemonade which was refreshing on a hot day and tasted delicious. To go with it, I stopped at Aldo’s Bakery and Coffee Shop and bought a tasty Oreo cookie that was a mix of soft and chewy with chunks of Oreos baked in.

Oreo cookie from Aldo's Bakery

Before dinner we headed down the stairs to Crescent Beach and walked along the rock jetty.

Crescent Beach, Block Island
Crescent Beach in Block Island

For dinner we chose the The Surf which is inside the Block Island Beach House. The inn was established in 1876 and gave off a New England seaside vibe mixed with a hipster feel. The restaurant sits on top of Crescent Beach and overlooks the ocean and harbor. We requested an outside table to take in the views and I ordered a caesar salad and a mac and cheese; both were exquisite. 

Block Island
The Block Island Beach House

Our fun-filled day flew by and before we knew it, it was time to leave the island. On our way back to the harbor we stopped in a few more boutiques where I purchased a bottle of tiny seashells, homemade chocolates, pins, a sea salt candle, and a postcard. I was searching for mementos that would remind me of my time spent on Block Island. As we left the harbor, we witnessed the most breathtaking sunset I’ve ever seen; it was one of those moments that makes you realize the best things in life are free.

Streets of Block Island
Sunset on the Block Island Express

A Walk Down Seaside Ave.

On our second to last day Billy and I took another stroll down Seaside Avenue. We stopped at West Beach where I had an ice cream from Hog Wild Smokin’ Cue.

Seaside Ave in Westbrook, CT
The Connecticut shoreline
Ice Cream at the Westbrook Connecticut Town Beach

Afterwards, we walked out to the rock jetty for a view of the coastline. Later on we continued our stroll through Pilots Point Marina and had an enjoyable lunch at a new restaurant called Liv’s Shack. I ordered a caesar salad with Parmesan truffle fries and Billy ordered a grilled cheese. We sat outside on the deck and watched the boats go in and out of the marina.

Pilots Point Marina in Westbrook, CT
Liv's Shack at Pilots Point Marina

After lunch we took a walk on the docks and it was interesting to see where all the boats came from—some traveled up the coast from as far as North Carolina and Florida. Being back at Pilots Point brought back memories of sleepovers in the clubhouse, midnight swims in the pool, boating with friends, and jet-skiing to Menunketesuck Island.

Pilots Point Marina on the Connecticut shoreline

Our Last Day

We had the cottage until 5:00PM on Labor Day so we had brunch at the Tea Kettle in Old Saybrook. Earlier in the week my sister and Hunter discovered this small diner and raved about their selection of one of a kind pancakes (cinnamon bun swirl + candied walnuts; brownie crumbles + chocolate sauce; apples, granola + brown sugar spice—there were so many variations it was hard to choose one). I ended up ordering the S’mores pancakes, and my mom ordered the Peanut Cup (both came with maple butter and powdered sugar), and they were out of this world. Thanks to Nicole and Hunter we have a new favorite breakfast eatery. Next year, I can’t wait to try the Strawberry Shortcake Pancakes; in the meantime, I’m going to attempt to create my own unique creations.

Tea Kettle Restaurant in Old Saybrook, CT

It was the second gloomy day out of the whole vacation and the water was pretty choppy due to Hurricane Dorian. I took tons of photos and videos to add my InstaStories. When I was a child a profound sense of sadness would come over me when my trip was ending. I thought that was something I had outgrown; but it wasn’t. After years of traveling and as much as I enjoyed each vacation, I would be eager to return to my life in L.A. However, during this vacation, I felt the same way I felt when I was ten years old and had to say goodbye to a place I love.

Seaside Ave, Westbrook CT
Waves at the Connecticut shoreline

We checked out and headed back to Massachusetts where Billy and I spent the night at my childhood home and caught a flight the next morning to head back to L.A.

I’ve been reminiscing about the wonderful summer I had, which began with a vacation to Arizona during Memorial Day weekend and then ended at this magical place on Labor Day. I’ve been home for over a week now and miss it even more. I’m counting down the days until we return next year. Here are some more of my favorite photographs…

The Connecticut Shoreline
A mermaid crafted out of seashells
Block Island
Yoga on the Connecticut shoreline
The Connecticut shoreline
Block Island
Candy at The Madison Beach Hotel Gift Shop
Date night
Block Island
Sunset at the Madison Beach Hotel
Beach day at the Connecticut shoreline

More Things To Do and See

There are so many places of interest at the Connecticut shore (you need a lot more than 10 days to conquer them all). Here are my recommendations on even more things to do, plus I’ve added a list of Block Island attractions.

The Connecticut Shoreline 

Where to stay:
Where to shop:
Where to eat and drink:
Salon & Spas:
Beaches:
More things to do: 

Block Island 

Where to Stay:
Where to shop:
Where to eat and drink:
Salon & Spas:
Beaches:
More things to do:

*This article contains some affiliate links.

Kristie Woszczyna

My life consists of writing, shopping, music, spending time with my boyfriend, working out, traveling and macarons from Bottega Louie. Kristie@a-girl-in-la.com.

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