History, and the Magic of the Season, on Display for the Holiday Tour of the Inns in East Hampton

The East Hampton area, including Amagansett, has long been known as a premier summer destination. Its pristine beaches, scenic farmland and farm stands, and vibrant restaurant scene have earned it a well-deserved reputation.

But there’s another side to East Hampton that shines in what’s often called the “offseason” — a quieter kind of magic that reveals itself in winter.

This December, for the second time, the Greater East Hampton Chamber of Commerce will present the Holiday Tour of the Inns, set for Saturday, December 13, from 1 to 4 p.m.

The tour — which carries a suggested $20 donation — features several inns throughout the Town of East Hampton in the full glory of their holiday décor. Must-see stops include The Baker House 1650, The Roundtree and the Reform Club in Amagansett, 434 on Main, The Huntting Inn, The 1770 House, The Maidstone, and Journey East Hampton.

Several local food establishments will also offer special discounts that day. Proceeds from the suggested donation directly support the Greater East Hampton Chamber of Commerce.

The inns on the tour showcase a rich mix of East Hampton’s finest — luxurious lodging, elegant dining, and deep local history. The event also offers visitors a rare opportunity to peek inside properties they may have only admired from the outside, experiencing their beauty, craftsmanship and holiday design firsthand.

The 1770 House is perhaps the most recognized of the stops. General Manager Carol Covell said last year’s event was a delight for guests and staff alike, and she’s thrilled to welcome visitors again this season to celebrate “the vibe and the magic” of the holidays.

“I truly enjoyed showing people around who had never been inside The 1770 House,” Covell said. “Everyone was kind and enthusiastic, feeling the magic of the holiday season.”

She added that many guests were surprised by what they discovered behind the historic façade.

“I saw so many people last year who had never come inside,” she said. “Now they know what it’s like, instead of just driving by on Main Street.”

Covell credits much of the inn’s festive charm to longtime head housekeeper Marcella Giraldo, who has led the decorating efforts since 2002.

“She is amazing,” Covell said. “She’s extremely particular about the Christmas tree — every branch has to be perfect. She knows exactly what she’s doing.”

Giraldo’s attention to detail and creativity transform the inn each December. The result is a stunning showcase that complements The 1770 House’s year-round elegance and storied past.

The property dates back to 1663, though most of its current features stem from the 1700s, when the Dayton family owned it. Dr. Jonathan Dayton lived there from 1764 to 1842; the home remained in the family until 1909, when the last Dayton resident — a widow said to have kept 127 cats — died.

During a 2002 restoration, staff discovered a handwritten note in a bottle penned by Mary Dayton in 1873 — one of the inn’s “beloved treasures.”

In 1942, John and Mrs. Williams purchased the property and created The 1770 House, preserving its colonial character.

“The inn has retained its colonial charm with some original architecture,” Covell noted. “For example, the handcrafted paneling in the reception area and one of the guest rooms reflects the Daytons’ sense of style and affluence.”

On December 13, guests will enjoy a self-guided tour that includes the inn’s historic tavern — complete with the remains of an old beehive oven — and, if rooms are vacant, a peek upstairs. Chef Michael Rozzi will offer an assortment of holiday cookies, and, of course, visitors can admire the inn’s beloved tree glowing with ornaments and lights.

“Everyone loves the tree at The 1770 House,” Covell said.

Just down the road, The Baker House 1650 offers another glimpse into East Hampton’s history and hospitality. Owner Antonella Bertello said she’s thrilled to once again open her doors to the community.

“We so enjoy welcoming our neighbors — from grandparents to grandkids,” she said. “They come to enjoy our beautifully decorated house and taste our wonderful cookies.”

Many families take their annual holiday card photos at the Baker House during the tour, surrounded by festive décor and live holiday music.

The inn also embraces the season outdoors, with cozy igloos on the patio, firepits for s’mores, and fondue under its “outdoor living room” — a canopy of 200-year-old wisteria vines, complete with warm blankets for chilly afternoons. Inside, the nine fireplaces in the main house and five in the Baker Carriage House will all be glowing, as guests sip hot chocolate and cider.

Built in 1648 by sea captain Daniel Howe, the house was sold two years later to Thomas Baker, one of East Hampton’s original founders, who turned it into Baker’s Tavern. Over the centuries, it has served as a meeting hall, community center, and site of the town’s first religious services.

In 1899, new owner James Harper Poor gave the house its distinctive English manor style. He later named it “As You Like It” in homage to his love of Shakespeare. In 1996, Gary and Rita Reiswig purchased the property from the Poor family and operated it as an inn for 30 years before selling.

A short walk away, The Huntting Inn is another East Hampton treasure. Built in 1699 as a saltbox home for Reverend Nathaniel Huntting, it stayed in the family for nine generations. The property evolved through many additions and renovations before becoming a boarding house, then later an inn. The Palm Restaurant Group purchased it in 1980 and continues to operate it today.

Steve Long, executive director of the East Hampton Historical Society, said each inn reflects an important chapter in the town’s story.

“What makes our community — and certainly Main Street — so special is its historical character,” Long said. “That’s what all of these inns celebrate, and preserving that is meaningful to them.”

He shared a few lesser-known facts, including that former East Hampton Police Chief Edward Morford once owned The 1770 House, where his wife ran a fireside waffle shop in the evenings. And in the 17th century, when Thomas Baker ran Baker’s Tavern, townsmen gathered there to debate what to do about Goody Garlick, the local woman accused of witchcraft.

The historical society offers a self-guided walking tour of Main Street, allowing visitors to learn even more about these storied properties. The Holiday Tour of the Inns, Long added, combines that local history with festive spirit.

“When people take this tour — and I hope lots do — they’ll come to appreciate, if they don’t already, the importance of our community’s historical character,” he said.