What's Changing at the Foot of Main Street in Sag Harbor This Fall?

On the morning of August 7, The Corner at 1 Main Street was supposed to open its doors again. A month later the restaurant was still dark, and the people who had planned to run it had moved on. Across the street at 2 Main Street, a sandwich shop that opened in mid-July is planning to stay open through February. Behind both buildings, the village has a signed contract for a waterfront boardwalk and a schedule to rebuild one of its municipal docks before the next boating season.

Taken one at a time, these are ordinary stories in a village newspaper. Together they show something new. Several different owners at the waterfront end of Main Street, and the village government too, are reshaping their piece of the block around year-round use. Most of that work falls between now and April.

1 Main Street: an empty room with a spring 2027 target

The Corner's story this year moved quickly. According to 27east's reporting, Kelly and John Piccinnini bought the business in February in partnership with Hildreth Real Estate Investors, the group that owns the building.

• February: The Piccinninis and Hildreth acquire the business.
• August 5 and 6: Friends-and-family lunches in the newly renovated restaurant.
• August 7: The planned grand opening is postponed that morning so the team can "fine-tune the details."
• September 3: The Piccinninis announce they are parting ways with the building's owners and will not open The Corner as planned.

In their statement the couple said their focus is now "100 percent on The Clam Bar and Sett Coffee." Hildreth said it "intends to keep The Corner active." It is also "looking forward to bringing in a new full-time tenant/operator to the space by the spring of 2027, if not sooner."

Any summer coverage that described a reopening is now out of date. As of today, 1 Main Street has no announced operator. The owner's stated goal is a full-time tenant, not a seasonal one. For decades under Jim Smyth, the 27east article notes, The Corner was an institution in Sag Harbor with an affordable, down-to-earth, family-friendly atmosphere. That is the standard any new operator will be measured against.

2 Main Street: a winter promise inside a building that may not last

The horseshoe-shaped building at 2 Main Street, known to many as Fort Apache, now has a new tenant beside K Pasa and Yummylicious. Cruust opened on Tuesday, July 14 in the space Espresso Da Asporto most recently occupied. Tip Top Hospitality, the team behind K Pasa and Sen, runs it. Ryunosuke "Jesse" Matsuoka and Bobby Deery, who was born and raised in the village, created the concept. The menu centers on sandwiches, salads, house-made pastas, and coffee, served directly on Sag Harbor Cove.

The owners call keeping Cruust open through the winter "a major priority." Deery put it plainly in the 27east piece: "We want this to be somewhere locals can grab lunch in February just as much as July." The team also said some Espresso-style classics may come back as a nod to the space's history. Off-season hours have not been published yet.

The building around Cruust is also up for review. 2 Main Street and 22 Long Island Avenue, the former 7-Eleven building, are now owned by Mavik Capital, a New York City real estate investment firm. Mavik was one of the original lenders when both properties sold in 2024 for a combined $30 million. Its plan, presented to the Sag Harbor Village Planning Board in September, would tear down both buildings. In their place would be a single 27,220-square-foot, two-story mixed-use development with a glass-covered walkway and promenade where the parking lot is now.

The proposal's own figures show how much would change:

The planned uses include three retail stores and three restaurants, one of them a rooftop restaurant with harbor views. There would also be space for a dry cleaner or cobbler, a professional office, a medical office, and a general store. Representatives from the Adam Miller Group, which is handling the application along with architect Chris DiSunno, said many current tenants in both buildings are committed to staying. They also said the owners will give priority to businesses committed to year-round operation when they fill open retail space.

The approval process will be long. The site is in the village's Historic District, the Waterfront Overlay District, and the Tidal Flood Hazard Overlay District. The project will need several variances, including parking variances, plus a full SEQRA environmental review. At the September meeting, Planning Board members raised concerns about the building's size and its effect on views. Nothing here has been approved. For now, Cruust's plan for winter lunches is going ahead inside a building whose future depends on a review that has barely begun.

The water side: a boardwalk contract and a dock on an off-season clock

The village's own projects fit the same pattern. On August 4, 2026, 27east reported that the Sag Harbor Village Board had voted unanimously to award the John Steinbeck Park Boardwalk Project to Chesterfield Associates for $1,032,070. The boardwalk will connect Windmill Beach, off Long Wharf, with John Steinbeck Waterfront Park on the other side of the Lance Corporal Jordan Haerter Veterans Memorial Bridge. It will be fully ADA-compliant. Local landscape architect Ed Hollander provided the landscape plan for Steinbeck Park and Windmill Beach free of charge. Former Mayor Jim LaRocca first championed the link, and Mayor Tom Gardella has made it a central priority. Grants cover most of the cost.

The details come from a separate Harbor Committee report:

1. An 8-foot-wide, pile-supported boardwalk on the landward side of the existing bulkhead along Windmill Beach and Steinbeck Park.
2. 400 square feet of gravel under the bridge on Ferry Road to join the two sections.
3. Twelve timber benches, set in pairs along the stretch near the windmill.

In August, construction was estimated to begin "this fall," so for now the boardwalk is a planned project with a forecast start.

A short walk west, "A" Dock at 11 West Water Street, past The Beacon, has a firmer timeline. The T-shaped, 20-slip dock dates to the 1970s. It will be replaced with a floating dock, along with a new bulkhead, boardwalk, and catwalk. The village swapped a planned timber railing for timber piles to keep views open. Construction is expected to begin in early November, after boating season ends, with the new docks ready for boats on April 1, 2027.

What the off-season calendar looks like from here

All of this work is timed for the quietest months. The calendar near the foot of Main Street is still busy, though, and the review meeting falls right in the middle of it.

Bay Street's season also includes Winslow: An Evening of Eagles on October 17, the Ha Ha Hamptons Comedy Tour on October 24, and a Think You're Funny? graduation show on November 24. Before the festival, Sag Harbor Cinema is showing The Fox and the Hound on October 17 and 18. Sense and Sensibility and You Can See Everything open October 16.

The Planning Board session on October 27 is the next public step for the largest of these projects. The Corner's next operator is still unannounced, and the boardwalk's start was forecast only as "this fall." The dock schedule is the only one with a fixed finish line. By April 1, 2027, the village plans to have new docks in the water at 11 West Water Street. Whether The Corner reopens by then depends on Hildreth finding its next operator.

As a twelfth-generation East Ender, I know the buildings at the foot of Main Street carry a lot of village history. If you'd like to talk about how changes like these fit into the bigger picture of Sag Harbor's historic district and waterfront, or what they could mean for a home nearby, I'm glad to help. Let's Connect with Jeanne Hutson.