The Oaks Waterfront Hotel has always had a quiet charm, but after a $10 million transformation, the storied property has emerged with a new identity — one that honors its past while embracing a sophisticated future.
Formerly known as The Pasadena Inn and later The Oaks Waterfront Inn, the hotel’s origins trace back to a time when it served as a humble country retreat. Ownership passed through several hands, including the Harper family, a German event company, and Candy and Paul Milne, who successfully operated it as a wedding venue for decades.
But when Tracy and Scott Wagner purchased the property in 2022, they had something more ambitious in mind: a complete reimagining of the inn as a boutique hotel and luxury event space.
“We saw what it could be,” says Andy Warner, co-owner of The Oaks and son-in-law to the Wagners. “It was beautiful, but it needed love, vision, and a serious investment.”
That investment came swiftly. The Wagners, joined by Warner and his wife Quin, closed the property in November 2022 for an extensive renovation. What followed was a top-to-bottom overhaul—a full gut of the original structure, the construction of 4 new luxury cottages, and a meticulous redesign of every room, ballroom, and common space.
The hotel reopened in May 2023 — just in time for a long-booked wedding.
Now, The Oaks Waterfront Hotel stands as a 15-room boutique destination, combining contemporary elegance with waterfront tranquility. Its vision is dual-purpose: a luxury retreat for travelers from New York, Washington D.C., Philadelphia, and Baltimore during the week, and a sought-after private wedding venue on weekends.
“We do about 25 to 30 weddings a year,” says Warner. “But when there’s not a wedding, we want this to be a getaway — where guests can come to relax, recharge, and enjoy a high-end experience in a small-town setting.”
The renovated rooms reflect that ambition: crisp whites, soft neutrals, and high-end finishes that channel a breezy, coastal calm. The interior transformation, led in part by Tracy Wagner with help from the design firm Bountiful, infuses light and space into what once felt like a timeworn country inn. Outside, the manicured grounds, flower beds, and a newly built dock bring the landscape into harmony with the elegance inside.
“There’s not a blade of grass out of place,” Warner laughed. “Our grounds crew is obsessive in the best way. And that’s what we want—perfection.”
Service is central to The Oaks’ new identity. “We’re family-run, and that means we’re here—every day,” says Warner. “My wife and I are on site constantly. My mom runs Guest Services. My in-laws walk the property weekly. It’s personal to us, and I think our guests feel that.”
What also sets The Oaks apart, particularly for weddings, is exclusivity. “When a couple books here, they’re getting the entire property to themselves,” says Warner. “There are no strangers roaming the halls. It’s theirs for the weekend. That makes for a different kind of celebration — more intimate, more memorable.”
The economic impact on Talbot County is notable. The hotel employs 25 full-time staff, and wedding weekends bring in an additional 25 to 30 local service providers. “These events bring people into town,” Warner said. “They stay at other hotels, eat at local restaurants, and shop in town. It’s not just about us—it’s part of a broader local ecosystem.”
The Oaks isn’t content just being beautiful. In 2024, the hotel was inducted into the prestigious Historic Hotels of America, a designation reserved for properties with significant heritage and character. It puts The Oaks in the company of storied landmarks like San Diego’s Hotel del Coronado.
“That was a big moment for us,” says Warner. “It’s not just recognition — it’s access to an audience that values authenticity and legacy.”
That blend of old and new defines The Oaks’ future. Warner says the team is focused on quality over quantity as demand for its weddings and lodging grows. “We may eventually shift to fewer weddings and more hotel guests,” Warner says. “But our goal remains the same: to be one of the finest boutique hotels in the region.”
Standing at the edge of the new dock as the sun sets over Oak Creek, it’s clear that The Oaks Waterfront Hotel is more than just a renovation. It’s a resurrection — of a legacy, a property, and a dream. For Warner and his family, it’s personal.
“This is home,” he says. “And we want every guest to feel like it’s their home, too—even if it’s just for the weekend.”
About Talbot County Department of Economic Development and Tourism
The Talbot County Department of Economic Development and Tourism’s mission is to enhance and promote a business-friendly environment for current and prospective enterprises and to advocate for policies that support and strengthen the economic vitality of Talbot County. The department’s vision for Talbot County is built on the principles of strong communities, empowered businesses, and innovative solutions.
Never Miss Talbot County Business News:
Subscribe to the Talbot Works newsletter here.
Wait! Before You Go!
Don’t forget to Explore Talbot County with us here.