Welcoming Rainy Simpson – Our new Executive Director


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After interviewing several qualified candidates we have hired a new Executive Director!

As sad as we are to have our founding Exec. Dir. Vickie Chambers retire, we’re excited to welcome Rainy Simpson to the position!

Happily Vickie will continue on to help with the transition, and make introductions of Rainy to our community.

After interviews our board felt Rainy was the best choice. Her life experience, understanding of our mission and the profound impact we have in our community (as a state supported historic Main Street town), seem made for a great fit.

Rainy spent much of her childhood visiting family in Coupeville and why she and her husband decided to move their own family here several years ago. Her husband works at Whidbey Health and their children attend Coupeville schools. Active in many aspects through fellow non-profits in our community, Rainy is especially proud of her work in our local schools, mental health and equality.

We thank our board members who lead the search and interviews for this very important position.

A few words from Vickie

Leaving after 10 years as Exec. Director of the Coupeville Historic Waterfront, I am so pleased to be able to transfer the office keys to someone able to maintain our unique district while developing new relationships and programs.  Rainy will join a full board of experienced, passionate members, and well-developed committees to carry on.

Our members are the best and I know they will work hard to make Rainy feel welcome and supported.

There’s so many to thank. Each of our members, partnering organizations, community leaders and citizens have helped to make CHWA the strong Main Street program it has become. CHWA represents a wide variety of interest and passions through our mission, and everyone’s participation has allowed us to focus on what is important and vital for our historic community’s well-being. 

It has been my honor and great joy to be a part of this Association.

  • Well, she’s hardly “..Outta Here!” – As we mentioned, Vickie will be helping with the transition and also the annual events we’re able to hold over the next year. She’ll be making introductions, happily on call, and of course we can always zip down to see her (through the summer and fall) and have a hot-dog when she’s working at her other job, Coupe’s Last Stand hot-dog stand!
  • Congratulations to Vickie’s husband, Randy, and their family! You’ll have much more time together and we promise to only borrow her now and then.

Rainy and Vickie – July 2021 – Two happy people who have the back of the Coupeville Historic Waterfront Association and our great community!

Executive Director Position OPEN at Coupeville Historic Waterfront


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Sadly our long time Executive Director Vickie Chambers is retiring. We hate to see her go, but are excited she will be enjoying more time with her family. Of course, because she’s a true blue community member, we’re sure she’ll be involved somehow with community efforts, and out and about in town like always.

As a certified Washington Main Street Organization within the Washington Department of Archeology and Historic Preservation this job has a heavy focus in our state designated “catchment area” which encompasses the several blocks flanking the historic waterfront of Coupeville and Penn Cove. You’ll be working in one of the most beautiful places on Whidbey and in our state as Executive Director of CHWA.

As a Main Street organization the Coupeville Historic Waterfront Association is a not-for-profit 501(c)3 and governed by a Board of Directors. The chosen candidate will work closely with our Board, our Membership and community partners.

We’re sad to see Vickie retire but excited for an opportunity to have another person devoted to our community take on this job as our Executive Director.

Peruse the Job Opening text, download the document, and please do share this with anyone you think may fit the needs of this position.

Download the Job Opening Document


JOB OPENING ED edit 6-22-2021


The Executive Director coordinates the creation and delivery of activities of Coupeville Historic Waterfront Association, a Main Street program utilizing historic preservation as an integral foundation for downtown economic development. The Executive Director encourages public awareness of and engagement with program activities and acts as a liaison to all committees and partner organizations. The Executive Director will serve as an advocate for the downtown and as an authority and source for information, resources and activities related to the revitalization initiative.


Coupeville Historic Waterfront Association (CHWA) is a 501(c)3 non- profit organization following the Main Street Approach® to downtown revitalization since 2008. Coupeville Historic Waterfront Association is a membership organization including business and residential members.

CHWA MISSION: To to strengthen, promote and maintain our successful historic district.

OVER-SITE: The Executive Director works under the President of the Board of Directors and reports monthly to the entire Board.


  • Supervises support staff, consultants, and volunteers
  • Bolsters membership
  • With the Board and its committees, helps sustain and or develop public awareness, educational programs and appropriate downtown revitalization strategies benefiting members and community
  • Marketing and or advertising CHWA events and programs at local, regional and state levels.
  • Recruiting and coordinating with volunteers to accomplish activities of board committees
  • Assists business and property owners with business and property improvement projects
  • Promotes cooperative partnerships between local businesses and fellow community organizations
  • Serves as an advocate for CHWA membership, and event and program issues at local and state level
  • Maintains data system tracking progress of CHWA programs
  • Attends and manages special events outside of regular business hours, including Washington Main Street conferences.
  • Grant writing
  • Assist board members and committees raising operational and event funding


  • Three to five years management experience
  • Experience working with boards and committees
  • Willingness to develop a thorough understanding of the Main Street Approach®
  • Self starter with an entrepreneurial, energetic, imaginative, and well organized spirit.
  • Capable of effective independent functioning
  • Excellent written and verbal communication skills
  • Ability to work with a variety of individuals and organizations building consensus among people of diverse skills and backgrounds
  • Proficiency in word processing, spreadsheets, and database management

COMPENSATION Salary determination to be based on qualifications.

HOW TO APPLY Please submit cover letter, resume and three references to Kathy Baxter, CHWA Board President
at president@coupevillehistoricwaterfront.com with subject line “CHWA ED Application”. Application must be received by June 23, 2021

There’s so much that’s wonderful about working at the Coupeville Historic Waterfront Association. You’ll be part of a dynamic business and residential community and participating is countless improvements and events along the historic waterfront. This job is for the community lover. A person who enjoys working hard for their members and extended community.

Maritime Washington National Heritage Area – Let’s ZOOM – May 6th


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As an Anchor Organization to the “Maritime Washington – National Heritage Area” we’re excited to see this public workshop opportunity! Join us for an educational and interesting time.


THURSDAY – MAY 6th – 5:00pm to 7:00pm

Through polls, group discussions and interactive features, Maritime Washington – National Heritage Area program staff will seek public engagement in discovering how best Maritime Washington – NHA could help serve the needs and futures of our unique waterfront communities.

During the main part of the workshop you’ll be able to share through polls, small group discussions, and other interactive activities. Workshop will focus on regional needs, priorities, goals and community takes and suggestions. 

Managed by the nonprofit Washington Trust for Historic Preservation, MW-NHA works to build partnerships and increase collaboration in order to support our coastal communities in celebrating, maintaining, and sharing their water-based stories.

Island and San Juan county residents register here for May 6th NHA workshop

Workshop is cost free. Pre-registration required

First half hour of the workshop will be an introduction to the program by program staff.

National Heritage Areas (NHAs) are designated by the United States Congress as places where natural, cultural, and historic resources make for a nationally important landscape.

MORE FAQ’s on Maritime Washington’s NHA designation

Over the next year Washington’s MW-NHA program will be working with coastal communities to chart a course for the MW-NHA based on community engagements. Throughout the first half of 2021, there will be lots of opportunities for waterfront citizens to share their views and ideas through virtual workshops, surveys, social media, focus groups,and more. These collaborative efforts will culminate in a MW-NHA management plan, which will serve as a framework for how we’ll work together for Washington’s maritime futures.

Coupeville helps anchor national Maritime Heritage Area – Whidbey Weekly

We’re off and running assisting those in need.


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Every year at the beginning of fall and throughout the holidays the Historic Waterfront organizes our Community Care Teams to gather greatly needed items to be distributed to local seniors, disabled adults and children in need. This year it’s especially important to up our offerings and we hope you can help, or share with someone who can.

Needed items listed below

Monetary contributions ARE tax deductible

ALL items purchased through your contribution, or purchased by you directly go to Island County Human Services. Their staff will make sure those most in need receive what Community Care teams have generated.

Our first 2020 delivery to Health and Human Services was received with great appreciation! 

Can you help us make the next delivery? YOU chose how to help. Give a monetary donation online right now and we’ll purchase assorted items from the list below, OR you can buy items from the list and bring them to the office. 

You can safely donate through paypal.

If you rather not donate online, mail a check to Coupeville Historic Waterfront, P.O. Box 121, Coupeville, WA 98239. Please put “Community Care” on the check’s memo. 

For drop off’s of items you’ve purchased from the list below, the CHWA office is located on Coveland behind and below Balanced Body Works – 6 Coveland – map. Dropped off items are ONLY collected October through December 19th. Monetary donations are taken year round.

IF the office is closed put your donations in the box outside the office door.

If you’re donating grocery, gas or gift cards you’ve purchased yourself, please email our Executive Director Vicky Chambers to arrange for a drop off or pick up. 


PLEASE – NO used items. 


Blankets/sleeping bags

Toilet paper

Kids tooth brushes/tooth paste

Adult toothbrushes/toothpaste

Diaper wipes

Grocery store gift cards (Red Apple or Safeway $10 each)

Gas gift cards ($10.00 each)

Laundry soapmanageable weight sizes please.

New socks (men’s crew/women’s)**greatly needed

New Underwear (men’s and women’s)

Paper towels


Adult wipes

Adult depends  

Feminine products

Cotton balls/Q-tips


Travel size shampoo/soap/deodorant/etc. personal hygiene items   

Bath towels/wash clothes

$ Quarters for laundromatGreat way to get the kids involved!!

Coffee cards/ fast food gift cards

Sweat pants and tops for men and women

Razors (male and female)

Plastic silverware/cups


Ziploc bags

Large garbage bags

Dog food/cat food/bird foodPet’s are family too

Hand and feet warmers

Clorox wipes

We are grateful to everyone who has a heart for those in need. Thank you!!!


CYBER Pumpkin Decorating Contest!


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Here we go! Time to bring Halloween pumpkin decorating into cyber space!

Along with 3 Sisters Market, the Coupeville Chamber, Island Transit, Rain Shadow Nursery and bayleaf, we’re sponsoring a cyber pumpkin contest

Paint or carve you’re pumpkin. Bring it down to the historic waterfront, take a picture on top of one of our hay bales, then LOAD IT UP to the contest’s website.

Oct. 17th through Oct. 27th load your pumpkins pics!

October 31st top 3 winners will be announced through Whidbey News Times

YOU’LL WIN PRIZES from downtown businesses!

In Coupeville YOU can get pumpkins at Sherman Pioneer Farm and Red Apple Prairie Center Market.

Sherman’s Pioneer Farm – 46 S Ebey Rd – map

Red Apple Prairie Center Market – 408 S Main St – map

Here’s some decorating inspiration from the Pumpkin Race!

We have canceled the Pumpkin race this year, but we’ll be back next year! Till then here’s some pumpkin decorating inspiration. For the cyber decorating contest you can carve or paint!