Join Oakcliff Sailing Center for their 4th Annual...

Spring Art Show & Champagne Brunch!

Party for the Grand Opening of Oakcliff's US Sailing Team Sperry Top-Sider Training Center!

Please join Oakcliff and US Sailing Team Sperry Top-Sider for the grand opening of their Training Center.  The party will be held on Thursday August 22, 2013 from 7:00pm to 1:00am at: 

Oakcliff's Clubhouse and Beach

2 South Street, Oyster Bay, NY 11771

Get Directions Here

Register Here!!

Harvest Regatta Celebration Returns on October 7

Oyster Bay, New York— The Oyster Bay Main Street Association and Oakcliff Sailing Center are joining forces again to host the Harvest Regatta Celebration on Friday, October 7, 2011. Last year's smashingly successful event will be duplicated. At 6:30pm a strolling dinner will be held in the quaint clubhouse and grounds of the Oakcliff Sailing Center at 2 South Street in Oyster Bay. Festivities will continue next door with live music and dancing, a unique silent auction, and showing of the work of the talented local artist Kirk Larsen that will be available for purchase.

The next day the signature Harvest Regatta will again take place in conjunction with the final Fall Classics Race. Costumes are strongly recommended. Regatta goers will have a chance to retrieve pumpkins from the water while sailing to win special prizes.



Several area restaurants will be providing food for the strolling dinner portion of the event. These include Coach Grill and Tavern, Christina’s Epicure, Jack Halyards American Bar & Grill, Luce Restaurant, Saggio’s, and Sweet Tomato. Bringing the “harvest” to the Harvest Regatta Celebration will be DelPozzo Foods from East Norwich. DelPozzo Foods participates in the Oyster Bay Farmers’ Market that is held downtown every Friday from 10am-4pm through October 28. They will bring their pastas, olive oils, balsamic vinegars, marinades, and pasta sauces to offer partygoers a taste of the farmers' market.

There are many businesses to thank for their role adding to the festivities. A wonderful selection of wine, beer, and specialty drinks will be provided. Wine has been donated by Testa Wines of Oyster Bay and Massican vineyard of Napa Valley. Mt. Gay cocktails will flow from the Boat Shed once again. Dodds & Eder has generously donated decorative plants for the night of the event. ENGEL & VÖLKERS of Locust Valley has sponsored printing of the event program.

Special silent auction prizes will include a sunset sail for four with Oakcliff Sailing Center and dinner at Jack Halyards American Bar & Grill; a house membership to Sagamore Yacht Club; an overnight stay at Oheka Castle; and various other fitness, health, spa visits, and dining auction items that people may bid on.

New this year is a ‘pick a prize’ raffle with a brunch for two at Rothmann’s, dinner for two at Wild Honey, and gift certificates to a number of area restaurants including Coach, Luce, Cafe al Dente, Canterbury's Oyster Bar and Grill, Serata, and Angelina's. If health and wellness is what you are looking for, maybe you can win a facial at Blue Water Spa or Shangri-La Spa, or treatments at Healthy Living Therapeutic. Promote your personal fitness with gift certificates from Bliss Studios and Evolution. Finally, fill your shopping needs with a gift certificate to Dodds & Eder, a gift basket from Chrison & Bellina, gift basket from Bon Vie, and a Utrecht gift bag and three complementary lessons at The Teaching Studios of Art.

The Oyster Bay Main Street Association is dedicated to enhancing and promoting an attractive and thriving downtown, while maintaining its historic integrity. We are a 501(c)3 Non-Profit using the national Main Street Approach® to downtown revitalization. Since 2001, we have been responsible for helping to attract over $30 million of investment to downtown Oyster Bay. This has led to the renovation of over 60 buildings, and the start of 57 new businesses in the downtown area. We manage a series of events throughout the year meant to promote the downtown and improve the quality of life including the Oyster Bay Farmers’ Market, the Oyster Bay Sundown Concert Series, and, new this year, Dancing in the Street.

Oakcliff Sailing Center was formed in 2010, to raise the levels of sailors and competitive sailing in the U.S. The Center is physically comprised of an America’s Cup-like campus in downtown Oyster Bay. The clubhouse, boat yard, and climate-controlled buildings house boat and sail storage, as well as rigging, composites, winch and hardware workshops. All of this is in close proximity to the commuter train station and a hundred yards from the Center’s deep-water docks and moorings.

Tickets are $75 in advance and $100 at the door. Tickets may be purchased securely online by visiting www.oakcliffsailing.org. Tickets may also be purchased by check, making this payable to OBMSA and sending this to PO Box 116, Oyster Bay, NY 11771. All proceeds are tax deductible and will jointly benefit the Oyster Bay Main Street Association and the Oakcliff Sailing Center.

Volunteers are needed to help the night of the event. For more information about sponsorship, tickets, or to volunteer please call (516) 922-6982 (516) 922-6982 or write oysterbaymsa@gmail.com.

Pearls of Oyster Bay Award Winners Announced

The “Pearl of Oyster Bay” was awarded to Sagamore Hill National Historic Site this week, one of 19 sites in the area elected by the community as a "Pearl of Oyster Bay". Sagamore Hill, family home of President Theodore Roosevelt, was designated a unit of the National Park Service System in 1962 and welcomes more than 50,000 visitors from the community and around the world who visit the Roosevelt Home and grounds each year.

Accepting the award on behalf of Sagamore Hill NHS are Thomas E. Ross, Superintendent and Sherry Justus, Chief of Interpretation, Visitor Services and Natural Resources. Pictured above left to right are Jerelyn Hanrahan, Artist of the Graduated Pearls Project , Sherry Justus, Tom Ross and Tracy Dellomo, Graduated Pearl Committee Member and Board Member of the Oyster Bay Main Street Association.

The sculpture project now has an underwriting sponsor, Superior Concrete of Brooklyn owned by local resident Constance Cincotta. The 20x40 foot pearl necklace sculpture will be cast in concrete supplied by Superior Concrete. The project has also been funded by an initial grant by the Oyster Bay Main Street Association and the New York Foundation for the Arts. The project, however is still in need of funding to bring it to completion. Interested donors should contact Jerelyn Hanrahan at Atelier Gallery 516-205-0907 for more information.

Other sites receiving recognition as "Pearls of the Community" in addition to Sagamore Hill, include The Waterfront, and Friends of the Bay. More "Pearls of the Community" still await to be announced.


Dawn Riley of Oakcliff Sailing Center and David Waldo of The WaterFront Center accept a pearl on behalf of the waterfront.



Pat Aitken, Executive Director, accepting a pearl on behalf of Friends of the Bay


Presentation of a pearl to Harriet Gerard Clark, Executive Director of Raynham Hall Museum.
Pearl presentation to William Miller and Mary Abbene of The Printery on West Main Street.

Another pearl presentation to Gooseberry Grove on East Main Street.

Nobman's Hardware accepting a pearl with Derrick Nobman, 4th generation to own and operate the business.
And, finally, St. Dominic's Chapel, another pearl of the community.

Classics Day Gives Free Admission to Attractions in Oyster Bay, Sunday, May 15, noon to 4pm

Classic Boats, Cars, Trains, and Cycles Too


A new exciting event "Classics Day in Oyster Bay " on Sunday, May 15, 2011, will take place at various locations in the hamlet from noon to 4pm. There will be a walking map with points of interest throughout the hamlet for the event.

Classics Day in Oyster Bay combines classic boats, classic trains, classic cars, and Billy Joel's classic motorcycles. It will be a nice day for people to walk around the town to relax; the kids can climb onboard a train; they can come to the water, see the boats and relax and have a drink. There will be no charge at any of the venues, and a great day to enjoy historic Oyster Bay.



Visitors will start at Sagamore Yacht Club where various classic boats will be on display, courtesy of Oakcliff Sailing Center and The Waterfront Center of Oyster Bay. Sagamore Yacht Club's decks provide breath-taking views of Oyster Bay Harbor.



From there, it is a short walk to the Oyster Bay Railroad Museum train yard, where guests may climb aboard restored cabooses and view several other types of train equipment.



Just around the corner is Oakcliff Sailing Center dedicated to training sailors, boat workers, owners and teams in order to raise the level of sailors and sailing in the United States.




Next stop, after walking through the downtown area of Oyster Bay, is Billy Joel's 20th Century Cycles. On display are a collection of some 60 bikes lined up in neat rows, each a story on its own, where the important icons of their day are well represented with names like Ducati, Yamaha, Honda, BMW, Royal Enfield, BSA, Triumph, Harley Davidson, Moto Guzzi and others.



Just across the street is the home of the Oyster Bay Railroad Museum, and then through Theodore Roosevelt Memorial Park back to Sagamore Yacht Club. The Sagamore Yacht Club will have steel drum entertainment providing live music the day of the event!



Participating restaurants will be offering Classics Day discounts throughout the day for those wishing to have lunch or dinner. For a full list of Dining and Shopping in Oyster Bay, visit the Oyster Bay Main Street Association website. Also follow us on Facebook at "Historic Oyster Bay" and on Twitter @oysterbayny.

Harvest Regatta Celebration Announced for October 8 in Oyster Bay

Oakcliff Sailing Center Clubhouse, 2 South St in Oyster Bay

Oyster Bay, New York— The Oyster Bay Main Street Association and the Oakcliff Sailing Center wish to invite the community to the first ever Harvest Regatta Celebration on October 8, 2010. The event will begin at 6:30pm with a strolling dinner in the quaint clubhouse and grounds of Oakcliff Sailing Center at 2 South Street in Oyster Bay. Festivities will continue later in the night next door with live music and dancing, a unique silent auction, and showing of the work of two talented local artists: Kirk Larsen and Bill Jonas. The Harvest Regatta to be held the following day (on Saturday) will showcase Oyster Bay’s beautiful classic yachts in their final race of the season.

Tickets are $75 in advance and $100 at the door. Online registration for the event is possible by visiting www.oakcliffsailing.org. Sponsorship opportunities are also available. Sponsors will receive recognition in the event journal and marketing materials.

Your contribution will help to support the important work of the Oyster Bay Main Street Association. Over the past decade OBMSA has improved over 40 facades and signs, over 20 businesses have opened, and several major grants have been attracted to improve downtown Oyster Bay. Several new events have also been started including the Oyster Bay Sundown concert series and the Oyster Bay Farmers’ Market that have been very successful at attracting new people downtown.

Oakcliff Sailing Center which will also benefit from the event was formed in 2010, to raise the levels of sailors and competitive sailing in the U.S. The center is based in Oyster Bay and has made an overwhelmingly positive impact on the village in the brief time they have been here.

Several businesses have generously provided their support. Those providing food will include Canterbury Ales Oyster Bar & Grill, Christina’s Epicure, Jack Halyards American Bar & Grill, Saggios, and Tex Mex Grill. Sagamore Graphics of Oyster Bay has sponsored printing of the invitation. Dodds & Eder has generously donated decorative plants for the night of the event.

Some of the auction items will include an overnight stay at Oheka Castle, antique and collectible merchandise from Coin Galleries of Oyster Bay, a Sunday bruch for four at Rothmann's Steak House, ballroom dancing lessons at Bliss Studios, a private performance by internationally acclaimed opera singer Anthony Pulgram, and a sail with Oakcliff and dinner at Jack Halyards American Bar & Grill. Gift certificates from AK Salon, Angelina’s of East Norwich, Evolution Fitness, La Pizzetta, Luce Restaurant, Shangri La Spa, The Coach Grill and Tavern, and Wild Honey have also been donated and will be provided for auction.

Tickets may be purchased securely online by visiting http://www.oakcliffsailing.org/. Tickets may also be purchased by check, making this payable to OBMSA and sending this to PO Box 116, Oyster Bay, NY 11771. All proceeds are tax deductible and will jointly benefit the Oyster Bay Main Street Association and the Oakcliff Sailing Center.

Volunteers are needed to help the night of the event. For more information about sponsorship, tickets, or to volunteer please call (516) 922-6982 or write oysterbaymsa@gmail.com.

Podcast of Oyster Bay Main Street Association 2010 Member Meeting

A Member Meeting for Oyster Bay Main Street was held the evening of April 15, 2010, at the Oakcliff Sailing Center. Presentations were made by President Ellen Roché and Executive Director. Guest speakers not included on this video include David Waldo from The WaterFront Center and Dawn Riley from the Oakcliff Sailing Center. For more information, please visit http://www.oysterbaymainstreet.org/.

OBMSA Mission
Oyster Bay Main Street Association (OBMSA) is dedicated to enhancing and promoting an attractive and thriving downtown, while maintaining its historic integrity. We are a 501 (c) 3 Non-Profit using the national Main Street™ Approach to downtown revitalization.

OBMSA Vision
The inviting gateways to Oyster Bay, including the waterfront, Route 106, and the LIRR, lead to an aesthetically pleasing historic downtown. Visitors and residents alike are impressed by the artistic and cultural attractions, including appealing diverse restaurants and shops. Walking through the downtown, one can view public art and a pleasing streetscape, which provides outdoor seasonal dining. Museums and an accessible waterfront provide an engaging family-friendly experience.

Main Street Announces Member Meeting & Formation of Advisory Board

Oyster Bay, New York – The Board of Directors of the Oyster Bay Main Street Association will hold a Member Meeting on Thursday, April 15, 2009, from 7-9pm at the Oakcliff Sailing Center, 2 South Street in Oyster Bay. At this meeting an update will be provided on the work of the board and committees. Featured speakers will discuss efforts underway to make Oyster Bay an internationally renowned sailing venue. Members of the public are welcome.

Main Street Member Meeting on April 15
Dawn Riley, the incoming Executive Director of the newly formed Oakcliff Sailing Center will speak on the work of her organization to make Oyster Bay an internationally renowned venue for training the next generation of competitive sailors in the U.S.

Prior to joining Oakcliff, Ms. Riley was the first woman to manage an America’s Cup sailing team and raced on four America’s Cup and two Whitbread (now Volvo Ocean Race) teams.

An update will be provided on the work of The WaterFront Center by their Executive Director David Waldo. Since joining the WFC in 2009, Mr. Waldo has developed new programs such as the Learn-to-sail in Sunfish program, an extra Survivors Program, and has worked to promote greater flexibility with existing rental services.

Mr. Waldo is an avid sailor who brings experience as a boat owner, racer, coach and head instructor at the Centerport Yacht Club.

Main Street President Ellen Roché, speaking of the meeting said: “This meeting is open to the public, though participants are encouraged to become a member, make a donation, and provide their opinion on how to improve Oyster Bay by visiting our website.”

People may RSVP for the meeting by visiting our Historic Oyster Bay fan page on Facebook.

Advisory Board Formed
The Main Street Board of Directors is also pleased to announce the meeting of a newly formed Advisory Board in early April. The Advisory Board will bring together significant community leaders to provide input on the work of the program. The purpose of the Advisory Board according to Organization Chair Bill Burke is “to provide broader insights, strategy recommendations and policy support to the organization.”

The Oyster Bay Main Street Association is a 501 (c) 3 Non-Profit dedicated to enhance and promote a healthy economy and maintain the attractive and authentic character in the historic downtown of the Oyster Bay Hamlet. OBMSA achieves these goals using the nationally accepted Main Street™ Approach to downtown revitalization. Since our founding in 2001, over three dozen projects have been completed, resulting in over $10 million of investment. For more information, or to become a member, please visit www.oysterbaymainstreet.org.