Spend a Perfect Day in Westerly, RI: A Dreamy Adventure Awaits!
- Kaylie
- Mar 2
- 6 min read
Updated: Apr 13
Explore the Charm of Westerly, RI
The "perfect day" outlined here is a whimsical journey through Westerly, Rhode Island. For those curious about the best spots in town and how to make the most of a summer day, this post is packed with insights. I will share links to my favorite businesses in hopes you'll find something delightful. Please note, I am not affiliated with any businesses mentioned, and I receive no commission from your clicks.
Join me as I take you through a day filled with joy, inspiration, and laughter! Perhaps you'll be encouraged to visit my charming hometown of Westerly, RI!
Introduction to Westerly, RI
Westerly is a small, coastal city in Rhode Island. This peaceful residential community transforms into a bustling hub during summer. Tourists flock here to explore the local beaches, Narragansett Bay, and the Rhode Island Sound. As the westernmost city on the coast, Westerly shares a border with Stonington, Connecticut, separated by the scenic Pawcatuck River.
Westerly is famous for its largest beach, Misquamicut Beach, and a vibrant dining scene. You can find a variety of seafood dishes and delectable Italian cuisine alongside live entertainment. The city has retained its historic charm, featuring many old buildings, including a real "downtown" area, where Matt and I enjoy our daily lives.
And let's not forget, Westerly is also home to the prestigious village of Watch Hill. This picturesque spot is where Taylor Swift's 1930 mansion, known as her "holiday house," overlooks stunning views of the Atlantic Ocean.
A Fictional Perfect Day in Westerly, RI
It's a Friday in June. My day begins around 7:30 AM. First, I feed my cat, Griffin, and tend to my "garden." This garden consists of a 4-tier Lettuce Grow hydroponic system and a 3-tiered planter. Both are carefully positioned on our compact 8'x12' balcony off the dining room.
Although our condo spans the 2nd and 3rd floors of a historic building, giving us no outside land for a traditional garden, I cherish our little balcony. After spending most of my adult life in bustling cities, this outdoor space is a breath of fresh air.
By the way, Lettuce Grow is fantastic! If you’ve been contemplating purchasing one, I wholeheartedly recommend it. It produces generous yields of lettuce, herbs, and vegetables, which my partner Matt and I truly appreciate. Our top crops include basil and parsley, and it's a joy to watch everything flourish.
After gardening, I prepare several Kaylie Dawn wholesale orders for shipment. For those unfamiliar, wholesale is how I supply my jewelry to retailers. I craft each piece in my home studio and ship bulk orders to stores, where they set retail prices. The feeling of knowing people across the USA—as well as in Canada and the UK—can enjoy my jewelry is remarkably fulfilling.
I truly enjoy packaging and shipping orders, finding it to be a rewarding endeavor. Most wholesale orders feature Anna bracelets, Jane bracelets, and Gemma II bracelets. With beautiful weather outside, I decide to walk to the post office for shipping instead of driving.
Along my route, I often see beautiful rhododendrons. This particular one is over 10 feet tall! It's hard to truly capture the splendor of Westerly's floral scenery in photos.
The United States Postal Office in downtown Westerly is a stunning marble building built in 1931. This architectural gem is listed on the National Register of Historic Places for its historical importance.
How could I resist a visit to Knead Doughnuts and Woodees, both just a short walk away? I indulge in a classic jelly-filled donut and chat with friends at Woodees while picking up a stylish new hair clip before heading home.
The day is leisurely, and I take my time walking through Wilcox Park. This stunning 14-acre Victorian-style park, designed by Warren H. Manning, lies just behind the Westerly Public Library. The flower garden is vibrant with color, showcasing blooming dahlias, peonies, and varieties I can hardly name. The library itself feels like a scene from Beauty and the Beast, with its regal structure seamlessly blending with nature.
I enjoy taking my time in the park, looking at all the flowers and watching the busy pollinators. Nature is truly mesmerizing.
Once I return home, I find that Matt is also done working. We grab our pre-packed beach bag, always ready by the door, and jump into Lapis (my '05 Hyundai Tucson) to head to Weekapaug Beach.
On our way, we take a scenic detour past the animals at Manfredi Farms.
With no traffic on the road, we stop at Sandy's Fine Food Emporium for two freshly-made sandwiches and a bag of Cape Cod chips. The Ashaway wrap is my personal favorite: smoked turkey, hummus, roasted red peppers, pepper jack cheese, tomatoes, and sprouts. Delicious!
Since it's a weekday, parking at Weekapaug is a breeze. We’re greeted by the friendly guard who waves as we walk down the short dirt road to the beach. I pull out an Elin Hilderbrand book and lose myself in its pages while munching on my favorite sammy. Life feels perfect.
After a few hours of blissful beach time, our water bottles are empty, and thoughts of dinner fill our minds. We pack up, not worried about sand in the car, and drive with the windows down past lookout cliffs and elegant summer homes. The air smells of sea salt, beach roses, and freshness. Taylor Swift plays on the radio, and we sing along.
Once home, I realize I don’t need much fussing with my hair (it's a perfect day, after all!). I take a quick shower, then slip into a sundress from Christina Ltd. I finish the look with my favorite straw flats and layer on some gold-filled bracelets as we ponder our dinner plans. It's a running joke that there are just too many great restaurant choices in town.
Should we dine downtown? We could go to The River Bar for my favorite sweet potato panang curry or head to Bird in Hand for something more sophisticated. The allure of dining at The Ocean House with its captivating views and impeccable service is strong. However, we decide to venture out, opting for waterfront dining at Dog Watch Cafe in Stonington.
Since we’re a bit early, we pop into Wm. Cole for a quick browse—a fantastic store for home goods and gifts. I chat with the owner over a glass of prosecco, and we share a laugh about my clutch and necklace; both treasures from her shop.
Amazingly, we score a perfect waterfront table at Dog Watch Cafe! My decision between the pizza salad and the chopped pasta salad is tough, but ultimately, the pizza salad wins. Paired with a refreshing glass of Sancerre, the evening feels just right. The sun sets slowly, and we remind ourselves it's Friday—two more days to enjoy! The atmosphere is vibrant, and everyone is in good spirits.
On our drive home, I remember there’s coconut cake waiting in the fridge. We savor two slices, change into pajamas, and settle in for a cozy movie night to cap off our perfect day.
What do you think of my dreamy day in Westerly, RI? Would you have chosen differently? So many options exist— (my dining dilemma proves it!)—perhaps a ferry or flight to Block Island? A scenic drive into Mystic? Endless activities can wait beyond the beach. Yet, this day embodies my ideal experience. I may need to draft more “perfect day” posts to highlight all the wonders Westerly has to offer. Thank you for sticking with me until the end—I'd love to hear your suggestions for next time in the comments!
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