On a Wednesday evening in July, the garden at Canoe Place Inn fills in around five o'clock. There's a band setting up under the string lights, glasses of rosé moving across the lawn, and neighbors who ten years ago would have needed a reservation in Southampton to get anything close to this. The scene isn't new because Hampton Bays suddenly discovered live music. It's new because for the first time, a resident can build an entire week here without ever pointing the car toward Montauk Highway west.
That's the actual story of this Hampton Bays summer. Not one flashy opening, but a calendar that finally has anchors on every night of the week, built from three new restaurants and one very old inn that decided to act its age in the best possible way.
The Building That Kept Failing Until It Didn't
If you've lived in Hampton Bays longer than a few years, you know the address at 149 West Montauk Highway even if you don't recognize the name on the sign anymore. It was Friendly's until 2017. Then it became Hamptons Standard in 2019, before a trademark dispute with the Standard Hotel group forced a rename to Salvatore's within the same season. Then came Barona Bay in 2023, a New American and European concept that didn't last the year. Three different restaurants, three different concepts, all in the same building, all gone within eight years.
Then Andrew and Evan DeRobertis signed the lease. The brothers grew up in the restaurant business, literally: their father, Paul DeRobertis, ran Paul's Italian Restaurant on Hill Street in Southampton for fifty years before selling it in 2023. When Andrew spotted a lease sign on the old Friendly's building in early 2025, he and Evan opened DeRo's Food & Family that spring, and they've since added a liquor license to a menu built around the kind of food a family orders on a Tuesday night, not a special occasion. The wall inside has panels dedicated to highlighting good deeds done by regulars. That's not a marketing gimmick borrowed from a corporate opening deck. It's what happens when the people running the restaurant grew up bussing tables in the same zip code.
The pattern matters more than the pizza. A location that had turned over three times in under a decade finally stuck, and it stuck because the people who took it over already had a customer base that included East Hampton, East Quogue, Riverhead, and Southampton, not just Hampton Bays. That's the kind of local proof no chain restaurant brings with it on day one.
Two More Names Locals Didn't Have Last Year
DeRo's wasn't the only new addition to the everyday rotation. Whale's Tale opened this season with a Southern California-style taco menu, the kind of place where you can grab a filet mignon taco or a bowl loaded with rice, beans, and plantains without dressing for the occasion. A few minutes away, Amalfi Coastal Kitchen & Cocktails took a waterfront spot and turned it into an Italian seaside concept, open for both lunch and dinner rather than the dinner-only model that a lot of Hamptons restaurants default to in summer.
None of this replaces what was already working. Sundays on the Bay on Dune Road has been the go-to for waterfront seafood and live music for years, and it isn't going anywhere. R.AIRE at the Hampton Maid still does Spanish tapas and paella under Chef Alex Bujoreanu, and Edgewater Restaurant still has the best deck view of Shinnecock Bay in town. What changed is the gap between those established, reservation-worthy spots and the truly casual end of the spectrum, the tacos-on-a-Tuesday or burger-with-the-kids kind of night. That gap used to mean driving toward Westhampton Beach. Now it doesn't.
The Inn That's Older Than the Country Got a New Chef
The other half of this story happened at the top of the market, not the bottom. Canoe Place Inn & Cottages traces its history back to 1697, and it markets itself, with some justification, as the oldest inn in the country. For most of its recent life, that history was the main draw. This year, the kitchen caught up to the reputation.
In May, Canoe Place introduced Michelin-starred Executive Chef Mathew Woolf, who unveiled a menu that includes a tomato tartare finished with burrata ice cream and a mushroom cavatelli built around wild mushroom ragu. The property is managed by Union Square Events, the hospitality group founded by Danny Meyer, which explains why the food now matches the setting instead of trailing behind it.
For a local, the chef announcement matters less than what came with it: an actual weekly program. Wednesday nights from 5 to 8 p.m., the garden turns into a live music venue for a series called Summer Sounds in the Garden, running from June 24 through September 2. Sundays bring brunch and a live DJ on the terrace at Good Ground Tavern, the property's tavern concept, from late morning into early afternoon. Mondays get an all-day happy hour followed by a 9 p.m. Industry Night with half off food and drinks, aimed squarely at the hospitality workers who keep the rest of the town running all season.
The Week, Mapped
Put the new restaurants and the reinvented inn together, and Hampton Bays now has something it didn't have a few summers ago: a night-by-night rhythm a resident can actually plan around without checking three towns over.
| Night | What's Happening | Where |
|---|---|---|
| Monday | All-day happy hour, then Industry Night with half off food and drinks after 9 p.m. | Good Ground Tavern, Canoe Place Inn |
| Wednesday | Summer Sounds in the Garden, live music from 5 to 8 p.m., running June 24 through September 2 | Canoe Place Inn |
| Friday | Weekly live music on the water | Cowfish |
| Saturday | Classic car nights and DJ sets by the bay | Tiki Joe's Meschutt Beach |
| Sunday | Brunch with a live DJ from 11 a.m. to 3 p.m. | Good Ground Tavern, Canoe Place Inn |
That leaves Tuesday and Thursday open for whichever of the newer dinner spots you haven't tried yet, which is exactly the point. A resident used to need a reason to leave town for a good night out. Now the harder question is which night to pick.
The Carnival Still Anchors August
None of this new energy replaced the parts of Hampton Bays that were never broken. The Hampton Bays Fire Department Carnival ran its usual five nights behind the firehouse on Montauk Highway in late July and early August this year, with rides from Blue Sky Amusements, carnival games, and a parade that's been part of the town's summer for longer than most of the new restaurants have existed. It's the kind of event that doesn't need a Michelin-starred chef or a rebrand to matter. It just needs to keep happening, and it did.
That's the real shape of the change here. Hampton Bays didn't reinvent itself this year. It filled in the parts that were missing while keeping the parts that were already working, and the result is a town where a Wednesday night and a Saturday morning both have somewhere specific to be.
What This Means If You Live Here
If you bought a home in Hampton Bays five years ago, you bought into a town that was still finding its footing between the flagship Hamptons villages and the quieter South Shore. This summer answered a question that had been sitting unresolved for a while: does the town have enough of its own gravity to hold a weeknight in place? Between DeRo's, Whale's Tale, Amalfi, and a three-hundred-year-old inn that finally has a kitchen worth the drive from three towns over, the answer this year was yes.
If you're weighing whether Hampton Bays still has room to change in ways that matter to daily life, not just property values, the honest answer is that it already has. The Hampton Edge Team works this stretch of the South Shore corridor every day and can walk you through what a specific block or neighborhood actually feels like to live in, not just what it looks like on a map. Reach out when you're ready to talk about what's next.
