Job Opportunities


JOB TITLE: Director of Nonprofit Programs and Affairs (“Nonprofit Director” or “NPD”) - FULL TIME

The Wayside Inn, doing business as The Wayside Inn Foundation (“TWIF”), is a nonprofit charitable Massachusetts corporation created in 1944 to own, operate, and maintain the Wayside Inn Historic Site, a campus of 9 historic buildings and over 100 pastoral acres. Our mission is to promote early American humanities and culture through hospitality, lodging, education, programming, and events, and continue an inn-keeping tradition dating back to 1716. Serving local communities as well as visitors from around the world, the site provides a unique, tranquil and historic setting rooted in colonial American traditions for family and friends of all generations to make lasting memories.

We seek to hire a highly qualified full-time professional to initiate, organize and execute programming, development and community engagement associated with our historic property that furthers the nonprofit identity and mission of the organization. These activities should both serve our existing constituents, and greatly expand our constituent base, increase visitation to and engagement with our beautiful historic site, and not least, broaden our base of “friends of the Inn” which will lead to increased public support.

Our current core operations comprise the historic restaurant, overnight lodging and event hospitality at Longfellow’s Wayside Inn for group events (weddings, celebrations and meetings). These facilities, functions and overall operations are managed by the Innkeeper, who reports directly to the Board of Trustees, a group of 10 volunteer trustees, responsible for the preservation and operation of the entire site. The Nonprofit Director (NPD) position described herein is a new and a separate role from core hospitality operations, representing TWIF and reporting directly to the Board of Trustees. However, the NPD will be required to work closely and collaboratively with the Innkeeper and staff to coordinate activities, resources, events and facilities use. The NPD will prepare and present status reports to the board at least quarterly, and participate in appropriate committee meetings (mainly programming, marketing/branding and development) as scheduled (presently, weekly).

The NPD will focus his/her time on furthering the nonprofit mission of TWIF, which is described in the institution’s mission statement above, through three main activities:  (A) Nonprofit Programming, (B) Development, and (C) Community Engagement.

A. NONPROFIT PROGRAMMING. Responsibilities include:
• Review existing programs and develop, propose and execute new and creative ideas compatible with our mission and resources to broaden our base of customers, guests, visitors and supporters
• Develop and submit an annual TWIF mission-relevant event calendar and manage all such events
• Manage all visitor experiences and feedback (relating to nonprofit programming)
• Take a fresh approach on historic preservation initiatives to support and leverage our historic assets (archives, collections, buildings, campus, etc.)
• Revitalize, develop and execute programs and activities celebrating American humanities, history, and culture (including art, music, gardening, poetry, architecture, cooking, etc.)
• Promote the self-sustaining principles which are historically rooted in the property
• Expand our portfolio of historic interpretation and educational activities
• Manage TWIF messaging, marketing and content on website and collateral
• Develop and manage TWIF programming budget
• Draw on inn’s rich history over 300 years and assets for themed programs and events (Howe, Longfellow, Ford, etc.)
• Work closely and coordinate with innkeeper on all TWIF activities and use of all buildings and sites for nonprofit programming
• Manage and conduct organized group history tours (on occasion as needed)
• Manage the preservation of, access to and use of archives and supervise archivist using best practices
• Review, update and ensure compliance with collections management policies; and advise board and obtain approval on any deaccessioning
• Manage, maintain and refresh exhibits in history/museum rooms, display cabinets, mill, schoolhouse and site signage to increase and enhance visitor experience
• Find and leverage ways for the institution to better tell its story and position its nonprofit mission
• Align TWIF programming and events with the board’s new branding/customer experience initiative
• Serve on the board’s programming committee and attend board meetings as requested

B. DEVELOPMENT.  Responsibilities include:
• Represent TWIF in all development/fundraising activities, in coordination with the board
• Develop, lead and expand relationships with foundations and other major donors
• Work with board on development goals, plans and execution of fundraising activities and events
• Manage fundraising events and calendar
• Identify and pursue grant and gift funding opportunities to support TWIF and its work (includes some grant writing)
• Manage any development consultants hired or retained to support development initiatives
• Work with the board to establish and implement a membership program with the objective of creating an ongoing support and revenue base
• Assist in the collection, compilation, curation and management of databases, including donors, visitors, and future visitors which can be leveraged for development, TWIF marketing and public communication
• Identify development opportunities that will drive fundraising and long-term and sustainable financial growth
• Utilize and leverage our unique assets (facilities, structures, fields, archives, collections, etc.) to strengthen revenue-generating events to endow our preservation fund
• Work with board and innkeeper to survey and monitor the preservation of historic assets (archives, artifacts, antiques, etc.) and facilities (buildings, trails, ponds, roads, etc.) and, as appropriate, seek and secure support for need-based gifts
• Work with board on long term development initiatives (“signature events”, capital campaigns, special gifts, endowment, etc.)
• Develop and manage a development budget and work with board on managing donations to and disbursements from designated development accounts/funds
• Manage development messaging and content on website and collateral
• Plan, implement and manage annual and special needs fundraising appeals
• Work with board to plan, implement and fund a new TWIF office for development, programming and community engagement
• Set goal to achieve a self-sustaining TWIF office, including NPD’s salary, within 3 years
• Serve on the board’s development committee and attend board meetings as requested

C. COMMUNITY ENGAGEMENT. Responsibilities include:
• Serve as board’s representative of TWIF and as the main point of contact for educational, recreational, historic, and cultural programming
• Develop and implement relationships with local, state, and national entities, organizations, and sites (e.g., Plimoth, Deerfield, Sturbridge, etc.) and cultivate partnerships, relationships and collaborative events to broaden awareness of the inn’s nonprofit programming and cross-marketing/member patronage
• Cultivate and expand relationships with state and local (Sudbury, Marlborough, Framingham, Hudson, Concord, Lincoln and Wayland) town departments, schools, senior centers, history centers, cultural societies, affinity groups (including colonial militia, heritage and genealogical organizations), scout troops, and other community groups and associations to increase site appreciation, visits, support and shared interests
• Support board’s re-branding and re-positioning campaign to increase TWIF’s profile
• Develop interpretative content and resources for visitors (signage, maps, spaces, etc.)
• Organize outdoor recreational and cultural events/pursuits which celebrate the expanse, beauty and social values of our historic setting, finding new ways to broaden four-season property use for public benefit and engagement
• Aid in the execution of a social media/ digital online presence and outreach campaigns to promote nonprofit programming and broaden community awareness
• Identify, collaborate and partner with organizations, individuals, and businesses including those outside of Massachusetts to benefit our development and branding initiatives
• Further organization’s mission and messaging through activities to increase visits and engagements with our campus, and not least, a broadening base of “friends of the Inn” which will lead to increased financial support from donors and foundations alike.
• Identify and increase community and public awareness opportunities to promote status of the TWIF and its nonprofit mission and programming
• Elicit, organize and manage volunteer corps to support nonprofit programming/operations
• Manage community engagement messaging and content on the website and collateral
• Develop and maintain a semi-annual newsletter that educates the public about the history of The Wayside Inn, highlights collections holdings, and provides information on programs and events.
• Serve on the board’s marketing and branding committee and attend board meetings as requested


• Demonstrated experience and success with the above core responsibilities (nonprofit programming, development and community engagement) in a similar role
• 5+ years historic site or museum management
• Experience building and leading a nonprofit department at a history-focused institution with collections
• Proven track record in development/fundraising
• Undergraduate degree in historic preservation, Early-American studies, Colonial architecture, or a related humanities field. Master’s Degree preferred
• Proficiency with museum management software and database management (eg., Past Perfect)
• Managing archiving practices, including collections, accession and deaccession policies
• Demonstrated ability to work collaboratively with MetroWest and Greater Boston-area nonprofits and the local business community
• Familiarity with Massachusetts and the MetroWest and Greater Boston-area grantor agencies
• Understanding of the Community Preservation Act and Town Meeting procedures helpful
• Given that the Inn resides in a local historic district, knowledge of local historic district guidelines and Massachusetts’ historic building survey and registration a plus
• Must have a comfort level working with and presenting to the town’s local governing boards
• Clear goalsetting and achievement metrics
• Ability to manage budgets and work efficiently and effectively
• Experience cultivating a volunteer program of students and community volunteers
• Strong local and regional community relationships
• Ability to engage and cultivate relationships with multiple and varied stakeholders
• Ability to work closely and successfully with nonprofit boards and staff
• Passion for American history, local culture, education, historic preservation, hospitality, and community engagement
• Highly professional, detail oriented and organized, with an ability to multi-task
• Super motivated, hard working, and committed to success
• Ability to bootstrap and be successful with goals by leveraging limited resources
• Able to develop a strong sense of “ownership” and identity with an organization
• High charisma and ability to nurture personal relationships
• Knowledge of Photoshop or other in-house marketing and design skills helpful
• Regular usage of social media to emphasize and brand build strongly desired
• Excellent written and oral communication skills
• Ability to work evenings and weekends as needed for committee meetings and programs

Annual Salary:  $50,000 - $55,000
Benefits: In addition to working in one of the most beautiful and cherished historic sites in Massachusetts with a deep sense of family, our employees enjoy a generous benefits package that includes: paid holidays, vacation time and sick days; group health and dental insurance coverage; disability and life insurance; voluntary 403(b) retirement savings plan participation; and complimentary employee meals.
To Apply: Please email a cover letter and resume to NO PHONE CALLS, please.


Longfellow's Wayside Inn is currently accepting applications for the following positions:

Kitchen Staff: Line Cooks, Prep Cooks, AM and PM shifts, some experience necessary, but will train the right person

Bussers: lunch and dinner

Host/Hostess: AM and PM shifts, experience preferred but will train the right person

Housekeeping: weekend and weekday shifts

Servers: Breakfast, Lunch and Dinner shifts, part-time or full-time. Experience preferred, but will train the right person.


Longfellow's Wayside Inn is part of the Wayside Inn Historic Site; a Massachusetts Historical Landmark, museum and an educational campus located on over 125 wooded and protected acres. We seek individuals who are flexible in schedule, punctual, and willing to work in a team-oriented atmosphere. Full and part-time, seasonal and year-round positions will be considered.

If interested in any of the above positions, please send resume or job inquiries to No phone calls, please.