THE VILLAGE
Westport Point
A historic harbor village at the tip of a peninsula in Westport, Massachusetts. Lobster boats, stone walls, folk music at the dock, and summer the way it used to be.
Summer 2026 — select weeks still available
About Westport Point
Westport Point is a village you find at the end of the road — literally. Main Road runs south through the town of Westport, Massachusetts, past farms and stone walls, narrowing as it crosses the causeway onto a small peninsula. At the tip, the road ends at a harbor where the east branch of the Westport River opens into Buzzards Bay. This is Westport Point.
The village has been here since the 1700s, when it was a working port for the whaling and fishing trades. That heritage is still visible in the architecture — Federal-era homes with widow's walks, Cape Cod colonials tucked behind hedgerows, and the kind of dry-laid stone walls that take generations to build. Lobster boats still work out of the harbor. The town dock is where fishermen unload their catch, kids crab off the pilings, and on Wednesday evenings in summer, folk musicians set up and play until the light fades. At 2042 Main Road, that music is about 100 feet from the front door.
What makes Westport Point different from the broader town of Westport, MA is its scale and intimacy. This isn't a place with shops and restaurants competing for your attention. There is an oyster bar on the harbor. There is Partners Village Store — half general store, half bookshop, entirely a gathering place. There is the dock. There are neighbors who wave from porches. And there is the water, everywhere you look. The village sits between two tidal channels, so you see the river from nearly every street.
After dinner, Main Road comes alive. Families stroll past the old graveyard, couples walk down to the docks to watch the light change, dogs trot ahead on the pavement. There are no sidewalks — you walk in the road, and cars slow down for you. The word for this place is bucolic — rolling, unhurried, gentle. The kind of quiet that makes you slow down without trying.
Staying at Westport Point means you're embedded in a real community, not parked in a tourist zone. The nearest beach — Horseneck — is a 10-minute drive. Westport Rivers Winery and Buzzards Bay Brewery are just up the road. Newport, Rhode Island is 30 minutes away. But the pull of the village itself is strong. Many guests find that a day at Westport Point — kayaking in the morning, walking the streets in the afternoon, oysters and folk music in the evening — is a day that doesn't need anything added to it.
What To Do at Westport Point
Wednesday Folk Music
Every Wednesday evening in summer, musicians gather at the fishing dock for an informal folk concert. Neighbors bring chairs. Some bring wine. From 2042 Main Road, you can walk down or just listen from the porch — the dock is 100 feet away.
Town Dock & Fishing Pier
The heart of the village. Watch lobster boats come and go, cast a line from the pier, or sit and take in the harbor. Kids crab off the pilings all summer. It's a short walk from 2042 Main Road.
Oyster Bar
A seasonal spot right on the Westport Point harbor. Fresh oysters, cold drinks, and a view of the boats. No reservations needed — walk over from the house and eat on the water.
Partners Village Store
Part general store, part bookshop, part community gathering place. Browse shelves of curated books, pick up local goods, and chat with the people who make this village what it is. Walking distance from 2042 Main Road.
The Evening Walk
After dinner, everyone walks. Up Main Road past the old graveyard, down to the docks, along the harbor. No sidewalks — you walk the road, cars slow down, and the pace is set by the tides, not a schedule. This is the main event at Westport Point.
Historic Architecture
Federal-era homes with widow's walks, Cape Cod colonials, and dry-laid stone walls that date back generations. Westport Point looks the way coastal New England is supposed to look — because it never stopped being that way.
Nearby Trails
Beyond the village walks, the broader town of Westport has trails through conservation land, working farms, and coastal forest. The Westport Land Conservation Trust, The Trustees, and the Buzzards Bay Coalition all maintain public trails a short drive away.
The Fire Pit
When the folk music fades and the harbor goes dark, the fire pit comes to life. This is where the day ends at Westport Point — at the edge of the water, under the stars, with the sound of the river and nothing else.
The Place
A Family's Place on the Water
The Long family has been at Westport Point for three generations. A grandfather who served thirty years as a Massachusetts State Representative. Letters from Senator John F. Kennedy — “Dear Representative and Mrs. Long” on Senate letterhead, a note signed “Jack” — years before he became the 35th President. A handwritten note from Senator Edward M. Kennedy. The kind of family archive that tells you something about the roots of this place.
2042 Main Road is where the family gathers — the boathouse, the dock, the fire pit, the backyard running down to the river. When you stay here, you're part of that tradition for the summer. This isn't an investment property. It's a family compound that opens its doors for the season.
From the family archive — Senator John F. Kennedy, before he became the 35th President
Frequently Asked Questions
What is Westport Point MA?
Westport Point is a small, historic waterfront village at the southern tip of a peninsula in the town of Westport, Massachusetts. It sits where the east branch of the Westport River meets Buzzards Bay. The village has its own ZIP code (02791), a harbor with working lobster boats, a fishing pier, and a handful of landmarks — including an oyster bar, Partners Village Store, and a tradition of Wednesday night folk music at the dock. It's a residential community, not a tourist destination, which is exactly what makes it special.
Is Westport Point the same as Westport?
No. Westport is a large, spread-out town on the South Coast of Massachusetts that covers farmland, rivers, and coastline. Westport Point is a specific village within the town — a tight-knit waterfront community at the very tip of a peninsula. Think of Westport as the town and Westport Point as its historic harbor village. When you stay at 2042 Main Road, you're in Westport Point, with all of greater Westport, MA just minutes away.
What is there to do at Westport Point?
Westport Point is built for slow summer days. Walk to the town dock and fishing pier to watch lobster boats come in. Eat oysters at the oyster bar overlooking the harbor. Browse books and local goods at Partners Village Store. On Wednesday evenings, folk musicians gather at the dock for an informal concert — bring a chair or listen from the porch at 2042 Main Road, 100 feet away. Kayak or canoe right from the property. The village is also a 10-minute drive from Horseneck Beach and the wineries of greater Westport, MA.
Can you walk around Westport Point?
Absolutely. Westport Point is a walking village. From 2042 Main Road you can walk to the town dock, the fishing pier, the oyster bar, and Partners Village Store. The streets are lined with historic homes, stone walls, and old-growth trees. There are no sidewalks — you walk in the road, and cars slow down for you. It's one of the best things about the village.
Where is the Westport Point oyster bar?
The oyster bar is on the harbor at Westport Point, within walking distance of 2042 Main Road. It's a seasonal spot right on the water where you can eat fresh oysters and watch the boats. No reservations, no fuss — just oysters and the harbor.
Are there vacation rentals in Westport Point?
There are a small number of vacation rentals in the village. 2042 Main Road is a 3-bedroom, 2-bath waterfront colonial directly on the harbor at Westport Point — an Airbnb with a 4.92-star rating, Superhost status, and a top 5% designation. It's available as a seasonal summer rental from June through August, with dock access, kayaks, and canoe included.
Stay at 2042 Main Road
Stay at 2042 Main Road — right in the heart of Westport Point. Book on Airbnb.
Book on Airbnb