The Oak Bluffs Association


Christine Todd, Executive Director

PO Box 1521,

Oak Bluffs, MA 02557

Phone: 774-563-9197

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The Oak Bluffs Association

Our Mission

The mission of the Oak Bluffs Association is to support a harmonious working relationship among members of the business community, civic associations, Town officials and the citizens of Oak Bluffs. We are committed to promoting the businesses, activities and attractions of Oak Bluffs in order to improve tourism through the pursuit of excellence, and in so doing, improve the quality of life for the community year round.


1. Develop our Membership.
2. Produce and distribute first-rate materials each year that will promote our events and members.
3. Find ways to extend the shoulder season business.
4. Work with organizations and Town officials to improve the Town and create a more productive and harmonious working relationship among all parties.


The Oak Bluffs Association has an extensive public relations program that helps to promote events both on and off island, helping to bring visitors to Oak Bluffs.

The OBA advertises in the local and regional media for all OBA sponsored events. Press releases and calendar listings are included as support for this program.

All members receive a listing with their membership, plus, links to your own web site are FREE. Only members may be listed, and the OBA web site is continually being updated.

The OBA also maintains and staffs the Information Booth at Farland Square in OB. Members are eligible to participate for free in the booth program. Non-OBA Members are also welcome to display their brochures, space permitting, for a fee.


Major events this year sponsored by the OBA include Harbor Festival, Tivoli Day, Wind Festival, Ladyfest, Small Business Saturday, Holiday Promotions.

All are welcome to participate in the Harbor Festival and Summer Solstice (mid-June) and Tivoli Day (mid-September) street fairs. Member-vendors, Vineyard artisans, and non-profits receive discounted fees for booth space.


OBA members are encouraged to attend the bi-weekly Board of Selectmen Meetings in an effort to improve working relations and communications between town officials and the business community and to address issues that may adversely impact the businesses of Oak Bluffs.



Membership includes:

Business listed on the OBA website with information

One brochure slot in the Information Booth

Promotion of your business on all social media channels

Regular correspondence pertaining to town business matters

Oak Bluffs event discounts

Representation, assistance, and support at official Town Meetings


$225 Full Membership

$125 Associate Member (Home Business or Non-Profit)

Membership is renewable each year.

Once your application is approved, you will be given access to the

Member's portal where you will be able to submit payment.



Dennis daRosa, President
daRosa’s Printing Co.
508-524-2065 cell
508-693-0110 work

Renee Balter, Vice President
Titticut Follies

Keith Enos, Treasurer
H & R Block
508-693-7722 work

Christine Todd, Executive Director
Oak Bluffs Association
PO Box 1521, Oak Bluffs, MA 02557

Doug Abdelnour
508-360-2703 cell

Holly Alaimo
Art Connection/MV Wind Festival
508-693-5444 work

Kathleen Cowley
Enchanted Chocolates

Kelly Feirtag
The Ritz Cafe

Jake Gifford

The Lazy Frog
508-693-4679 work

Ana Ilievska
Rockland Trust Bank

Terry McCarthy

Dockside Marketplace
239-591-0836 cell
508-693-3392 work

John Newsome

Lawrence Realty
774-274-0066 cell
508-693-3302 work

Mike Santoro

Lookout Tavern, The Ocean View, Fishbones
508-274-0716 cell
508-693-7129 x. 11 work

Ann Smith
Featherstone Center for the Arts

John Tiernan

Dockside Inn
508-693-2966 work

Michael Wallace

Budget Rent-A-Car
508-693-0236 work