a history of
Hospitality
From the start of The Avenue Restaurant as a “tea room” in 1937 to the recent renovations of Cooper Cottages, Seaboard Hospitality has flourished over four generations by identifying what customers want most in vacation accommodations and amenities and delivering it with an emphasis on caring, thoughtfulness and value.
Our History
Early Roots in Hospitality
“Big George” Shockley was a serial entrepreneur who dug and dredged canals, salvaged and sunk ships, bought and sold real estate, and built a variety of commercial and residential buildings.
He and his wife, Eliza, got their start in hospitality first constructing and then renting vacation cottages in Rehoboth Beach on the ocean block of New Castle Street where they also made their home in a boarding house, renting out rooms on the upper floors.
That early venture into the nascent tourism industry in Delaware soon resulted in the building and operation of a movie theatre and a “tea room” on Rehoboth Avenue in 1937.
Early Roots in Hospitality
“Big George” Shockley was a serial entrepreneur who dug and dredged canals, salvaged and sunk ships, bought and sold real estate, and built a variety of commercial and residential buildings.
He and his wife, Eliza, got their start in hospitality first constructing and then renting vacation cottages in Rehoboth Beach on the ocean block of New Castle Street where they also made their home in a boarding house, renting out rooms on the upper floors.
That early venture into the nascent tourism industry in Delaware soon resulted in the building and operation of a movie theatre and a “tea room” on Rehoboth Avenue in 1937.
After a short lease to a third party, the Shockleys acquired additional parcels of land behind the property to expand the business in the 1940s.
Soon thereafter, they turned the whole of the space over to their daughters, Grace and Helen, to operate with Helen’s husband, Alvin, as the Avenue Restaurant.
Grace later left the partnership to focus on vacation rentals, taking over from her parents the reservations and operations of more than a dozen rental cottages. She oversaw their upkeep and maintenance during the offseason and the tasks of greeting, checking in, and seeing to any ancillary needs of guests during the high season.
Grace was especially fond of hosting the frequent returning guests of the cottages and made many friends of the visitors who considered their annual summers in Rehoboth part of their own family tradition.
Meanwhile…
Over the same time, and only blocks away, Helen and Alvin kept up the daily operation of the Avenue Restaurant for breakfast, lunch and dinner nearly 365 days out of the year. Helen was a constant fixture in the front of the restaurant, greeting diners and escorting them to their seats, while Alvin oversaw operations in the kitchens and set the guest menus.
During their tenure, the couple expanded the restaurant from its humble tea room origins to a 400-seat facility with three dining rooms, a lobby and bar, three serving kitchens, a back commissary and a bakery. Loyal patrons of the restaurant flocked back to its offerings year after year, and many bragged of waiting up to two hours to eat at the landmark site.
Building on to and otherwise maintaining the properties passed to them by their father, the Shockley and Simpler heirs laid the groundwork for their own children to take over the vacation cottage and restaurant businesses, ushering in a third generation committed to a tradition of coastal hospitality.
Establishing the Hotel Footprint
Ken Simpler, the son of Helen and Alvin, began working for his parents at the Avenue Restaurant in the 1960s and ran it continuously through the late 1980s. A restless entrepreneur in the mold of his grandfather, “Kenny” invested profits from the restaurant into a variety of businesses. He first bought and remodeled an apartment building on the beach, following that with the construction of beachfront townhomes and a later foray into several coastal housing developments. In the midst of these ventures, Kenny built the 35-room Atlantic View on the oceanfront in Dewey Beach in 1978, and in so doing cashiered his hospitality roots as a restauranteur to that of a hotelier.
Sam Cooper, Grace Shockley’s son, and Kenny Simpler joined forces in 1980 to build a second hotel, the 38-room Beach View, on land originally acquired by their grandfather near the boardwalk in Rehoboth Beach. While Sam remained responsible for the cottage rental business on New Castle Street, he was a mostly silent partner in the new hotel venture as he had staked his career in elected office, becoming first a Rehoboth city commissioner in the early eighties before taking on a nearly 30-year tenure as the Town’s longest-serving mayor.
Based on the successes of the Atlantic View and Beach View hotels, Kenny Simpler determined to expand his hotel holdings outside of Delaware. In 1984, he built and opened the 60-unit Surf Side Hotel in Nags Head, North Carolina on beach front parcels he had long admired while fishing in the Outer Banks. Only a few years later, he added a south building to serve as an additional set of efficiencies to the hotel.
The North Carolina projects were succeeded by another out of state venture in 1987, when Kenny acquired a derelict motel property on the oceanfront in Cocoa Beach, Florida. The former “Islander Motel” was renovated and expanded into a 55-unit boutique bed and breakfast and relaunched as The Inn at Cocoa Beach.
Kenny Simpler capped an impressive foray into the hotel business by deciding to end the nearly 50-year run of the Avenue Restaurant in the mid-1990s. Returning to his hospitality roots, he razed the building his grandparents had built and his parents had operated and built in its place an homage to them, retaining the iconic Avenue name, but transforming the property into a 50-unit hotel. This venture culminated in the opening of the Avenue Inn & Spa in 1996 and capped off the family’s initial footprint in the hospitality sector as the Simpler Hotels Group.
Entering a New Era of Expansion
Three generations of Shockleys and Simplers set the table for a fourth generation of owner-operators to carry on their legacy. Kendra (Simpler) and Alex Moore worked closely with Kenny Simpler in the operations of the Atlantic View and Beach View before taking an active role in the design and construction of the Avenue Inn & Spa. Ken Simpler, Jr. started with his father at the Avenue Restaurant before participating in the construction and first year of operations of the Surf Side Hotel.
Together, Ken and Alex formed the Simpler Hotels Group’s first management company, the predecessor to Seaboard Hospitality. Under their stewardship, the management company has expanded its ranks to include executive office positions for operations, finance and facilities, and established its corporate headquarters just outside Rehoboth Beach.
Over the same time period, Alex and Ken continued to develop the hotel portfolio, acquiring several properties to the west of the Avenue Inn, including a small, 12-unit hotel that now operates as a satellite “annex.” Major renovations to the main Avenue property in 2012 were followed by a significant expansion onto the newly acquired lots in 2016. Together, these improvements have nearly doubled the size of the original hotel and provided for a world class set of amenities.
Today at Seaboard Hospitality
More recently, the Seaboard team has undertaken renovations to the vacation cottages originally built by the first generation of Shockleys and lovingly maintained by the subsequent two generations. The first phase of Cooper Cottages opened in the summer of 2021 with the second phase following in June of 2022. Initial reviews from guests have been overwhelmingly positive about this unique offering.
Today, Seaboard is positioned to grow on the Company’s roots in hospitality established nearly a century ago. Three projects to renovate and expand existing properties are in the concept and design stages and outreach and due diligence are ongoing for potential additions to the portfolio.
The Seaboard team continues to grow, and even as its ranks expand beyond its families’ foundings, the values in which it is rooted remain vibrant and guiding: create special places for guests to stay and enjoy.
Four Generations of Hospitality
1930s-1960s
- 1930s: land purchased in the ocean block of New Castle Street in Rehoboth Beach to build nearly a dozen vacation cottages and a boarding house
- 1937: a theatre and tea room constructed on Rehoboth Avenue, eventually giving over the entire space to operate as the Avenue Restaurant
- 1945: lots on Wilmington Avenue acquired to expand the Avenue Restaurant
- 1940s: vacant land acquired in the ocean block of Wilmington Avenue to build vacation rental units
- 1960s: land adjacent to the Avenue Restaurant on Rehoboth Avenue acquired to expand, nearly doubling seating capacity to 400 persons
1970s-1990s
- 1976-78: land acquired and construction of Atlantic View Hotel on the beachfront in Dewey Beach
- 1980: construction of the Beach View Hotel on Wilmington Avenue site originally purchased for vacation rental units
- 1985-87: land acquired and construction of the Surf Side Hotel on the oceanfront in Nags Head, North Carolina
- 1990: land south of and adjacent to the Surf Side acquired and 16-unit satellite addition constructed with indoor pool
- 1990: derelict hotel property acquired on oceanfront in Cocoa Beach, Florida and renovated and expanded into The Inn at Cocoa Beach
- 1992: hotel properties first treated as a portfolio under the name Simpler Hotels Group
- 1995: derelict hotel property acquired on oceanfront in Cocoa Beach, Florida and renovated and expanded into The Inn at Cocoa Beach
- 1995: formation of Simpler & Sons, LLC, the legal predecessor to Seaboard Hospitality
2000s – Present
- 2005: launch of Seaboard Hotels as the dba name for the group
- 2010: 12-Unit Sea Esta Hotel acquired on Rehoboth Avenue and re-launched as the Avenue Annex, a satellite to the Avenue Inn
- 2012-14: four additional lots acquired to the north of the Avenue Inn on Wilmington Avenue
- 2012: Avenue Inn ground floor parking garage renovated into modern lobby, breakfast, area, fitness room and spa
- 2016: Avenue Inn expanded by 28 units on two of the three lots acquired north of the hotel
- 2021: Opening of first phase of Cooper Cottages
- 2022: Second phase of Cooper Cottages
Establishing the Hotel Footprint
Ken Simpler, the son of Helen and Alvin, began working for his parents at the Avenue Restaurant in the 1960s and ran it continuously through the late 1980s. A restless entrepreneur in the mold of his grandfather, “Kenny” invested profits from the restaurant into a variety of businesses. He first bought and remodeled an apartment building on the beach, following that with the construction of beachfront townhomes and a later foray into several coastal housing developments. In the midst of these ventures, Kenny built the 35-room Atlantic View on the oceanfront in Dewey Beach in 1978, and in so doing cashiered his hospitality roots as a restauranteur to that of a hotelier.
Sam Cooper, Grace Shockley’s son, and Kenny Simpler joined forces in 1980 to build a second hotel, the 38-room Beach View, on land originally acquired by their grandfather near the boardwalk in Rehoboth Beach. While Sam remained responsible for the cottage rental business on New Castle Street, he was a mostly silent partner in the new hotel venture as he had staked his career in elected office, becoming first a Rehoboth city commissioner in the early eighties before taking on a nearly 30-year tenure as the Town’s longest-serving mayor.
Based on the successes of the Atlantic View and Beach View hotels, Kenny Simpler determined to expand his hotel holdings outside of Delaware. In 1984, he built and opened the 60-unit Surf Side Hotel in Nags Head, North Carolina on beach front parcels he had long admired while fishing in the Outer Banks. Only a few years later, he added a south building to serve as an additional set of efficiencies to the hotel.
The North Carolina projects were succeeded by another out of state venture in 1987, when Kenny acquired a derelict motel property on the oceanfront in Cocoa Beach, Florida. The former “Islander Motel” was renovated and expanded into a 55-unit boutique bed and breakfast and relaunched as The Inn at Cocoa Beach.
Kenny Simpler capped an impressive foray into the hotel business by deciding to end the nearly 50-year run of the Avenue Restaurant in the mid-1990s. Returning to his hospitality roots, he razed the building his grandparents had built and his parents had operated and built in its place an homage to them, retaining the iconic Avenue name, but transforming the property into a 50-unit hotel. This venture culminated in the opening of the Avenue Inn & Spa in 1996 and capped off the family’s initial footprint in the hospitality sector as the Simpler Hotels Group.
Entering a New Era of Expansion
Three generations of Shockleys and Simplers set the table for a fourth generation of owner-operators to carry on their legacy. Kendra (Simpler) and Alex Moore worked closely with Kenny Simpler in the operations of the Atlantic View and Beach View before taking an active role in the design and construction of the Avenue Inn & Spa. Ken Simpler, Jr. started with his father at the Avenue Restaurant before participating in the construction and first year of operations of the Surf Side Hotel.
Together, Ken and Alex formed the Simpler Hotels Group’s first management company, the predecessor to Seaboard Hospitality. Under their stewardship, the management company has expanded its ranks to include executive office positions for operations, finance and facilities, and established its corporate headquarters just outside Rehoboth Beach.
Over the same time period, Alex and Ken continued to develop the hotel portfolio, acquiring several properties to the west of the Avenue Inn, including a small, 12-unit hotel that now operates as a satellite “annex.” Major renovations to the main Avenue property in 2012 were followed by a significant expansion onto the newly acquired lots in 2016. Together, these improvements have nearly doubled the size of the original hotel and provided for a world class set of amenities.
Today at Seaboard Hospitality
More recently, the Seaboard team has undertaken renovations to the vacation cottages originally built by the first generation of Shockleys and lovingly maintained by the subsequent two generations. The first phase of Cooper Cottages will open in the summer of 2021 with a second phase to follow in the spring of 2022.
Today, Seaboard is positioned to grow on the Company’s roots in hospitality established nearly a century ago. Three projects to renovate and expand existing properties are in the concept and design stages and outreach and due diligence are ongoing for potential additions to the portfolio.
The Seaboard team continues to grow, and even as its ranks expand beyond its families’ foundings, the values in which it is rooted remain vibrant and guiding: create special places for guests to stay and enjoy.
Four Generations of Hospitality
1930s-1960s
- 1930s: land purchased in the ocean block of New Castle Street in Rehoboth Beach to build nearly a dozen vacation cottages and a boarding house
- 1937: a theatre and tea room constructed on Rehoboth Avenue, eventually giving over the entire space to operate as the Avenue Restaurant
- 1945: lots on Wilmington Avenue acquired to expand the Avenue Restaurant
- 1940s: vacant land acquired in the ocean block of Wilmington Avenue to build vacation rental units
- 1960s: land adjacent to the Avenue Restaurant on Rehoboth Avenue acquired to expand, nearly doubling seating capacity to 400 persons
1970s-1990s
- 1976-78: land acquired and construction of Atlantic View Hotel on the beachfront in Dewey Beach
- 1980: construction of the Beach View Hotel on Wilmington Avenue site originally purchased for vacation rental units
- 1985-87: land acquired and construction of the Surf Side Hotel on the oceanfront in Nags Head, North Carolina
- 1990: land south of and adjacent to the Surf Side acquired and 16-unit satellite addition constructed with indoor pool
- 1990: derelict hotel property acquired on oceanfront in Cocoa Beach, Florida and renovated and expanded into The Inn at Cocoa Beach
- 1992: hotel properties first treated as a portfolio under the name Simpler Hotels Group
- 1995: formation of Simpler & Sons, LLC, the legal predecessor to Seaboard Hospitality
2000s – Present
- 2005: launch of Seaboard Hotels as the dba name for the group
- 2010: 12-Unit Sea Esta Hotel acquired on Rehoboth Avenue and re-launched as the Avenue Annex, a satellite to the Avenue Inn
- 2012-14: four additional lots acquired to the north of the Avenue Inn on Wilmington Avenue
- 2012: Avenue Inn ground floor parking garage renovated into modern lobby, breakfast, area, fitness room and spa
- 1995: derelict hotel property acquired on oceanfront in Cocoa Beach, Florida and renovated and expanded into The Inn at Cocoa Beach
- 2016: Avenue Inn expanded by 28 units on two of the three lots acquired north of the hotel
- 2021: Opening of first phase of Cooper Cottages; second phase to follow in 2022
JOIN THE SEABOARD HOSPITALITY
Crew
We are always on the lookout for people who can build on our history of hospitality. If you would like to help us carry Seaboard Hospitality forward in its next 100 years, we invite you to explore opportunities to join us.