20 Best Things to Do in Westport, MA

Tucked away on the southern coast of Massachusetts, this quiet town holds a wealth of beauty and unique experiences that I'm excited to share with you.

From the tranquil beaches to the rich historical sites, the vibrant local culture to the lovely vineyards, an array of delights is waiting to be discovered.

Prepare to be captivated as I guide you through some of the best things to do in Westport, Massachusetts!

Enjoy Strolls on Gooseberry Island

Have you ever visited places that take your breath away?

For me, it's Gooseberry Island.

As the day's first light grazes the sky, I often find myself already on the beach.

There's something irresistible about feeling the sand beneath my toes and the fresh, salty breeze that gently tugs at my hair.

I can affirm that it lives up to the reviews you might've read online.

With only a handful of cars, the beach is a serene escape.

And the best part?

No fee to enjoy nature's marvels.

June is my favorite month.

It's when the island turns into a little slice of heaven.

I've witnessed some of the most beautiful sunsets here.

The sky becomes a passionate artist's canvas, painted with orange, pink, and purple hues.

It's a sight that can make even the most mundane day seem magical.

If you ever plan to visit this island right off the coast of Westport, don't forget to bring your bug spray.

Once you're off the coast, the bugs can be pretty bothersome.

But don't let that deter you.

The stunning views from the island's river and ocean side are worth it.

There's also a boat ramp and port-a-potty available.

I usually love walking down the paths around the island with my dogs.

It's never too crowded, giving us ample space to enjoy our walk.

The rustling of the leaves, the chirping of the birds, and the distant sound of waves crashing against the rocks - it's therapeutic.

Gooseberry Island is an experience that reminds me how beautiful life can be, one sunrise at a time.

Go on Paddling Adventures at Sea Kayak Connecticut

The splendor of a serene Sunday spent paddling down the Saugatuck River is truly something to treasure.

My partner and I decided to soak in the last bits of summer by renting a double kayak from Sea Kayak, Connecticut.

We were greeted by a team of friendly faces, ready to equip us with everything we needed for our three-hour adventure.

One thing that immediately stood out was the quality of the kayaking equipment.

It was clear that this place values top-notch gear, ensuring a smooth and safe journey for all its patrons.

We arrived 15 minutes early, eager to embark on our journey, and true to their word, we were on the water precisely on time.

As we paddled downstream, the picturesque landscape unveiled a pleasing array of local wildlife.

The calm water mirrored the tranquil sky above, adding to the overall idyllic experience.

Moreover, the convenience of online booking also made this trip a breeze to plan, making impromptu trips on the river a regular part of our weekends.

They've created a welcoming space for everyone - whether you're a seasoned paddler or utterly new to the sport.

The added benefit of two-person crafts is an absolute win, especially for families with younger kids.

Apart from top-notch services, the location offers easy parking, clean restroom, and changing facilities.

So, if you're in the mood for a beautiful day out on the water, look no further than Sea Kayak Connecticut - it's truly a local gem.

Explore the Allens Pond Wildlife Sanctuary

What can I tell you about the Allens Pond Wildlife Sanctuary that the chirping of birds, rustling of leaves, and silence of the vast open spaces won't convey better?

I am blessed to live near this sanctuary and enjoy its beauty almost daily.

My morning routine invariably includes a hike through its well-maintained trails.

The paths are perfect for a tranquil walk, with the verdant expanses around me and the soft crunch of leaves beneath my boots.

Some areas can get a bit muddy, especially after rain, so remember to wear good hiking boots when exploring.

A walk here is like a live nature documentary, with salt marshes and pristine beaches painting a beautiful, serene picture.

This place is a paradise if you're an avid birdwatcher like me.

Seeing ospreys soaring in the sky is just, well, breathtaking.

It's a fantastic experience to witness these magnificent birds in their natural habitat.

I've also enjoyed spotting various shorebirds during my numerous visits.

It's a sight that still leaves me stunned, regardless of how many times I've seen it.

I highly recommend a visit to anyone who appreciates nature, wildlife, and tranquillity.

The sanctuary is an experience - a reminder to slow down and appreciate the wonders around us.

It is one of the most beautiful places in Massachusetts, and I can say with certainty that a visit here would leave you refreshed, rejuvenated, and renewed love for nature.

Enjoy a Serene Retreat at Dedee Shattuck Gallery

Our town has an unspoken rule - when you need to escape the hustle and bustle, you take a detour to the Dedee Shattuck Gallery.

This haven of tranquility, nestled slightly off the beaten path, offers an extraordinary art selection and breathtaking landscapes that speak directly to your soul.

Walking into this spacious gallery is like stepping into another world.

The high ceilings and perfect light filtering through the windows create a magical aura that enhances the artwork.

Some days, I lose track of time as I navigate through thought-provoking exhibitions by early computer artists.

On other days, I sit by the window, engrossed in a book, while the calming view of the charming surrounding landscape unfolds outside.

But the Dedee Shattuck Gallery is also a fantastic venue for events.

I still remember the excitement that filled the air when my friend held his wedding ceremony on the lush lawn outside the gallery.

Laughter and cheers echoed throughout the venue as guests indulged in a clam bake and danced under the dimmable lights within the gallery.

It was an unforgettable experience, a testament to the versatility and charm of this lovely space.

Whether you're an art enthusiast or just looking for a peaceful retreat, this gallery should be on your list.

A journey to the Dedee Shattuck Gallery is a journey into beauty, creativity, and tranquility.

Enjoy a Peaceful Escape at Westport Town Farm

One of the things I love about living here is that whenever life gets overwhelming, I can always escape to the serenity of Westport Town Farm.

This place is an absolute paradise for nature lovers like me.

The walking paths here are as soothing as they are well-maintained.

A certain tranquility engulfs you as soon as your feet hit the gravel.

What I enjoy the most about this place is the melodic symphony of songbirds.

Sitting, listening, and letting the chirps and trills wash over you is so soothing.

It's like my concert, set against the backdrop of lush green fields.

While there's a lack of facilities at the farm, I feel it just adds to the rustic charm of the place.

There's no urban noise or interference, just the sweet symphony of nature.

The charm of Westport Town Farm lies in its simplicity.

It's a gentle reminder of the peace and tranquillity that can still be found amidst our chaotic lives.

Sample New England at Westport Rivers Vineyard

I've always had a soft spot for wineries and their tranquil ambiance.

Nestled in the heart of New England, Westport Rivers Vineyard has been a sanctuary for me, offering a unique wine experience that truly represents the region.

Over the years, I've seen the vineyard evolve.

They've kept their offerings fresh, adding new wines to their collection.

While some of them are not my favorites, they still exemplify the unique character of the region's terroir.

But the charm of Westport Rivers Vineyard is not limited to the taste of their wines.

The surroundings are simply breathtaking!

It's a picturesque view of New England's countryside with well-maintained vines stretching as far as the eye can see.

They've also started inviting food trucks, which perfectly complement the outdoor venue and provide a wonderful treat after a wine tasting.

And remember that the vineyard is well kept and clean, even their bathrooms.

They've ensured that your experience is about the wines and the overall atmosphere and comfort.

But the sweeping views, the tranquility it provides, and the chance to sip wines that embody New England's essence keep me coming back for more.

Discover Nature's Charm at Old Harbor Wildlife Refuge

Who'd have thought I would find such a hidden gem in my backyard?

Without a doubt, Old Harbor Wildlife Refuge has become my regular sanctuary.

Located near Westport, it's a captivating portal to nature's beauty, all within reach at westportlandtrust.org.

My first escapade here led me to well-marked trails that weave through the refuge.

It's a two-hour journey that promises tranquility and adventure at every turn.

The longest trail covers nearly three miles, ideal for a deep dive into the forest's heart.

Likewise, the mix of single-track and double-track trails makes it even more exciting.

While the single track offers a fun, runnable path, the double way presents unique challenges.

Partially frozen in winter, it's uneven with tractor tracks, turning the trail into a thrilling escapade.

Old Harbor Wildlife Refuge isn't just about the trails, though.

It's a treasure trove for the adventurers at heart.

Hidden within its premises is a geocache, a test for the true explorer.

Despite my best efforts, I still haven't located it.

But that doesn't deter me; instead, it's an enthralling mystery that keeps me returning.

Some areas can get a bit muddy, but it's all part of the rustic experience.

I can't wait for summer to experience the trails in a new light.

Old Harbor Wildlife Refuge is a testament to the serene and wild beauty that Westport has to offer.

It's my go-to place for solitude, adventure, and communion with nature.

Appreciate the Simplicity of the Hix Bridge Boat Launch

Every chance I get, I make a point to visit the Hix Bridge Boat Launch.

There's something about the quiet simplicity of this place that draws me in.

It's an escape from the bustling city life.

Nestled in the heart of Westport River, it's a convenient spot for boaters like me.

Whether a lazy Sunday morning or a bright, sunny afternoon, this place offers seamless access to the tranquil river.

The view of the water has a calming effect on me, instantly melting my stress away.

Likewise, the added security gives me peace of mind, knowing my vehicle is safe while I enjoy my time on the water.

Plus, the process of acquiring a permit is relatively straightforward.

For fellow boating enthusiasts, I strongly recommend you visit this hidden gem.

Don't just take my word for it; experience it yourself.

I'll see you at the Hix Bridge Boat Launch!

Enjoy Beach Days at Horseneck State Reservation Campground

I've always had a soft spot for Horseneck Beach State Reservation Campground.

This sprawling landscape is a treasure trove of nature's wonders - offering the perfect wind-surfing conditions, an estuary for bird-watching, and trails that make you fall in love with the great outdoors.

As a kid, I remember the beach being my favorite playground.

Over the years, it has seen lots of updates.

But the vibe of the beach remains the same - it's blissful, serene, and always inviting.

The water can be rough at times, with a two-foot drop.

But the thrill of the waves, the salty air, and the charming seagulls more than make up for it.

Plus, the bathrooms are always clean.

If you love a bronze tan, this is the place for you.

I have tried various beaches in the area, but none gives me a tan as good as Horseneck.

Trust me, just lay in the sun for a few hours, and you'll have a golden glow with people asking where you've been vacationing.

However, remember that the sand disappears on the campground side during high tide.

And, if you're not from Massachusetts, the entrance fee can be a bit steep.

But believe me when I say that the experience is worth every penny.

After all, Horseneck Beach State Reservation Campground is all about preserving the natural beauty and tranquility of the area.

So, enjoy a day (or more) at this stunning beach and let the beauty of nature wash over you.

Spend the Day in Gooseberry Neck, Westport

I'll never forget the day I first moved to Gooseberry Neck.

It was a place that felt like home from the get-go.

Imagine a place where the water is warmer than anywhere else in Massachusetts, and the sunsets are breathtaking.

That's Gooseberry Neck for you.

I started my day like usual, with a brisk bike ride around the area.

Something about biking through the winding roads of Gooseberry Neck gets my adrenaline pumping.

One of the best things about this place is the proximity to nature, and what better way to experience it than on a bike ride?

After a good amount of biking, my stomach usually starts to rumble.

It's time for my favorite part of the day – lunch at The Bay Side.

This is where I indulge my taste buds in some of the best cuisines.

The top-notch food and the ambiance are just right, making it the perfect place to unwind after a long morning.

As the day begins to wind down, there's one more thing that I always look forward to – watching the sunset.

There's something magical about how the sun dips below the horizon, casting a warm glow over everything.

The view of the sunset from Gooseberry Neck is spectacular, and it's something that should be on everyone's bucket list.

Sure, life in Gooseberry Neck might seem like a dream, and that's because it is.

It's a place that offers so much, from natural beauty to food and people.

And it's this unique combination that makes it truly special.

Enjoy a Tranquil Day at The Knubble Beach

Imagine waking up to the rhythmic waves lapping against the shoreline, the seagulls singing their morning tunes, and the salty breeze soothing your senses.

The beach is always clean, making it a perfect spot for early morning strolls.

Its quiet ambiance provides an ideal escape from the hustle and bustle of city life.

There's something serene about listening to the rustling leaves and the distant sound of waves crashing against the rocks.

One of my favorite activities at The Knubble is fishing.

Just a few hundred feet away, there is a dock where I spend hours casting my line into the calm, rippling waters.

The joy of catching the first fish of the day is truly unmatched.

Moreover, the dock also serves as an excellent place for a quick swim.

The water is always calm and inviting, making it a favorite spot for locals and visitors alike.

And let's not forget about the picturesque landscape.

The Knubble is a canvas where nature paints its most beautiful shades.

Quite a few couples choose this stunning location for their engagement photo shoots.

The magical sunsets, the sparkling waters, and the dreamy skies make for a perfect romantic backdrop.

Whether you're a fan of beach activities or you crave some peace, The Knubble never disappoints.

Whether pulling a boat ashore or picnicking with your loved ones, there's always something to do here.

For me, there's no better place to call home.

Uncover History at Westport Historical Society

One sunny Saturday, I decided to indulge my curiosity and explore the past.

The Westport Historical Society, a place quietly tucked away in the heart of my town, beckoned me with its old-fashioned charm.

Stepping into the historical society was like stepping into a time machine.

The old building, with its creaking wooden floors and smell of old books, had a certain magnetism that immediately drew me in.

As I wandered through its rooms, each filled with trinkets and treasures from our town’s history, I was transported back to a time before computers, before cars, when life was simpler, and every object had a story to tell.

Their collection is vast and varied, ranging from old photographs and newspaper clippings to ancient artifacts and household items that were everyday necessities in their time.

The items were carefully curated and arranged in a way that told the story of our town from its humble beginnings to its present day.

Each exhibit was thoughtfully laid out, and the narrative was not just read but experienced.

One of my highlights was the interactive displays – a clever blend of technology and history.

I watched the interactive videos, played the vintage games, and even tried my hand at some old-world crafts.

It was engaging, informative, and indeed brought history to life.

The Westport Historical Society is a community hub.

They organize many events, from historical lectures and workshops to town celebrations and children's programs.

I’ve attended a few of their events.

Each was a wonderful experience that allowed me to connect with my neighbors, learn something new, and gain a deeper appreciation for the history of Westport.

Visiting the Westport Historical Society wasn't just an educational afternoon.

It was an immersive experience, a leap back in time, and a testament to our town’s rich history and vibrant community.

This place shines brightly in the heart of Westport, enriching the lives of its residents and visitors alike.

Enjoy the Day at Horseneck Beach

There's nothing like starting your day with a refreshing morning walk along Horseneck Beach.

The sensation of cool sand and pebbles under your bare feet is simply indescribable.

It uniquely blends a low-key coastal recreation area and a natural wonder with its fantastic dune trails.

One memorable experience was a day when the clouds were so low they practically touched the ground.

It felt like we were enveloped in a soft, misty blanket all day.

The gentle breezes added a soothing touch, making it an unforgettable day.

The tides can be pretty high, but boards are placed in various spots to keep you safe.

Early mornings are incredibly serene.

The beach opens at dawn, and the low tides are calm at that hour, creating a peaceful ambiance.

The waves can get rough on certain days, making it an exciting spot for wave-watching.

Horseneck Beach is also a haven for local bird species.

As a frequent visitor, I appreciate the conservation efforts taken here.

Sure, there are rules - no drinking, no dogs, no smoking, and no surfboards or flotation devices - but these are in place to preserve the tranquility and natural beauty of the area.

Whether you're a fan of early morning walks, bird watching, or want to escape from the hustle and bustle of daily life, this beach has something for everyone.

While lounging on the sand and listening to the rhythmic echo of the waves, you'll find it easy to understand why I and many others love spending time at Horseneck Beach.

Visit Westport Point

Waking up to the salty breeze of Westport Point can feel like being on vacation every day.

The charm of this quaint seaside town, nestled in the heart of Massachusetts, is something that words can't adequately describe.

When you set foot in Westport Point, you feel an immediate sense of calm and tranquility.

My mornings often start with a walk along the scenic shoreline, the morning sun casting a golden hue over the Atlantic.

The peace and solitude of this place is simply breathtaking.

It is a paradise for nature lovers, offering ample opportunities to spot diverse wildlife.

From playful seals to majestic ospreys, the variety of creatures that call Westport Point home is truly remarkable.

The afternoon is best spent exploring the town's rich historical heritage.

The Westport Point Historic District, with its antique homes and charming cobblestone streets, is a throwback to a bygone era.

And if you're a history buff like me, you'll love visiting the Westport Point Wharf.

This historic site offers a glimpse into the town's vibrant maritime past.

Come evening, nothing is better than settling down with a good book at the local coffee shop or indulging in fresh seafood at a waterfront restaurant.

The sunset views from the dining patios are nothing short of spectacular.

Westport Point is an untouched gem that perfectly blends tranquility and charm.

I promise you won't be disappointed!

Other Things to Do Nearby

Enjoy the Day at Round Hill Town Beach

Round Hill Town Beach embodies the true spirit of a beach day.

There's something magical about the beach that keeps calling me back.

One windy day, the lifeguard was kind enough to help me with my beach bag and even chased my hat when it flew off.

Parking here is a breeze, and they even provide special beach wheelchairs for those who need them.

I've seen many times when someone drives up and is immediately available for use.

It's best to call ahead, though, to make sure they're available.

My little ones love looking for hermit crabs on the far right of the beach.

The calm cove with no waves and soft sand entry is perfect for them to play safely.

There's even a food truck on the far left, but remember to bring cash, as they don't accept cards.

Like any place, Round Hill Town Beach is close to my heart.

Whether you're a local or just passing by, a day at this beach is well spent.

Discover History at Fort Rodman

One of the gems in my hometown is Fort Rodman, an imposing waterfront fort with a rich Civil War history.

Whenever I get free time, I love to wander around its old, crumbling walls, imagining what life must have been like for the soldiers who once lived there.

Inside, it all looks a bit abandoned, but I find it oddly charming in a rustic way.

The fort's exterior is just as intriguing, if not more.

There are sections of the fort outside where you can thread through a labyrinth of old bunkers.

Visiting feels like stepping into a time capsule.

Don't miss the beautiful boardwalk nearby, adorned with a series of benches offering breathtaking coast views.

I often strolled along the paved trails, soaking in the peace.

The area also boasts playgrounds, beaches, fields, and even an outdoor shower near the bathrooms.

While the ice cream shop only opens on Saturdays and Sundays, it's a treat worth waiting for.

Nothing beats enjoying a scoop of your favorite flavor while watching the sunset over the sea.

Visit the adjacent military museum to delve deeper into the fort's history and explore various historical artifacts.

Fort Rodman is like a living history book, offering a peek into our past while reminding us how far we have come.

It's a must-visit if you're ever in town.

Enjoy a Delightful Experience at Running Brook Vineyard & Winery

Stumbling upon a hidden treasure is never bad, and that's precisely what I found in the Running Brook Vineyard & Winery.

One day, I decided to explore a bit more, and that's when I discovered this wine haven nestled in my backyard.

As soon as I walked in, the place's rustic charm and inviting atmosphere instantly lifted my spirits.

It felt like a home away from home.

My eyes were met with an impressive selection of wines and brandies, all calling out to me.

I decided to dive right in with a tasting session.

Each pour was a melange of flavors, the wines and brandies expressing a unique story.

A highlight for me was their rosé and brandy.

The rosé perfectly balanced, dry, and sweet, while the brandy was smooth and rich.

It was a treat to discover that they provide tastings and flights.

This allows everyone, even a novice like me, to find something they love without feeling overwhelmed.

Running Brook Vineyard & Winery, with its exceptional wines and inviting atmosphere, is a gem that deserves more recognition.

It's proof that you don't always have to look far to find excellent quality - sometimes, it's right in your backyard.

Walk around Demarest Lloyd State Park

Wait until the tide is low, then lace up your trusty water shoes for a refreshing walk along Demarest Lloyd State Park's shoreline.

I strongly recommend this walk for its beautiful views and peaceful atmosphere.

Starting from the large parking lot, I walk eastward, almost half a mile down the road, to the smaller parking area.

Then, it's on to the beach, where the first part is rocky but still teeming with life, especially during low tide.

Children, in particular, will have a blast spotting guppies, crabs, and periwinkles in the shallow water - I know I did when I was a kid!

As I continue my walk, the rocks gradually give way to a sandy riverbank at the mouth of the Slocum River.

This is my favorite spot in the park, with its soft, fine sand and clear water.

It's a bit of a trek, but oh-so-rewarding when you finally sink your feet into the warm sand.

On the other hand, if you're looking to swim in deeper water, you might find the park's shallow waters a bit limiting.

But, for those like me who relish basking in the sun with their feet in the water, Demarest Lloyd State Park is a heavenly retreat.

If you have a pet, the park is even more appealing because dogs are welcome on the beach - a rare treat for pet owners like me.

Remember to keep some cash on hand for the parking fee.

Wander the Trails of Freetown-Fall River State Forest

Strapping on my trusty hiking boots, I set out from my doorstep, ready for another day of exploration in my backyard playground, the Freetown-Fall River State Forest.

Lush, green, and teeming with life, this massive expanse of public land is a nature lover's paradise.

My friends and I often spend our afternoons traversing its 50+ miles of dirt trails, every bend revealing another fascinating piece of the forest's puzzle.

The abundant life in the forest is just part of the allure; the brook, stocked with trout, is a haven for anglers.

Casting a line and sitting back to enjoy the serenity is a pastime I've come to cherish.

It's a moment of tranquility amidst the world's rush.

The forest isn't only about solitude, though.

Come summer, it transforms into the ultimate family picnic spot.

The wading pool attracts a crowd of kids, splashing around and laughing while their parents shop on the picnic grounds.

The lively, communal atmosphere adds color to the forest's green tapestry.

But what truly sets this forest apart is its mystical aura.

The Bridgewater Triangle, with its stories of pukwudgies and other strange occurrences, adds a sense of intrigue.

While I can't say I've encountered any legendary creatures, I've certainly stumbled upon the odd, strange noise during my evening walks.

It's all part of the forest's charm, though.

Every step you take, every trail you follow, you're participating in a living, breathing story unfolding for centuries.

Whether you're after a peaceful retreat, an active adventure, or a brush with the supernatural, Freetown-Fall River State Forest offers it all.

Thanks to its blend of rich history, natural beauty, and community spirit, it's a treasure trove waiting to be discovered.

Final Thoughts

The charm and beauty of Westport, Massachusetts, is something you have to experience for yourself.

Whether it's the draw of the undulating vineyards, the allure of the sprawling beaches, or the call of the wildlife that ropes you in, there's no denying that Westport has a truly unique charm and a rich tapestry of experiences to offer.

Each day spent here is a testament to the town's irresistible allure, and I can't wait to see what new adventures tomorrow will bring.