Legendary Tales. Timeless Opportunities.

Join The Wayside Inn team and become part of the history of American hospitality. 

Join a Winning Team.

Longfellow’s Wayside Inn is part of The Wayside Inn Historic Site and is the oldest operating inn in the United States. We are always looking for outstanding talent to join our team for the following positions:

  • Director of Finance:
    The Wayside Inn seeks a proactive, dynamic and experienced Director of Finance to join its team to be responsible for a wide range of financial and administrative management responsibilities. Reporting to the Innkeeper and working with the Director of Community Engagement and other department managers, as well as the Board of Trustees, the Director of Finance must be a strategic and disciplined thinker who will provide strong, innovative financial stewardship, grants management, account management, and fiscal oversight. The Director of Finance ensures strategic implementation of long-term strategic goals. The Director of Finance will serve as a resource on all financial and some operations matters. The incumbent assists the Innkeeper with oversight of all financial, operational and administrative activities. The new Director of Finance will also be expected to serve on the Board’s Finance and Development Committees, which meet bi-monthly. The Inn’s annual sales are approximately $4.5M with about 40 full time employees and 50 part time employees. The Inn’s day-to-day operations are managed by the Innkeeper/General Manager and the Director of Community Engagement manages development, programming, and community relations, both of whom report to a Board of Trustees. The position reports to the Innkeeper, is full-time (40 hours/week, Monday through Friday). 
    See the complete list of duties and qualification requirements here. E-mail cover letter and resume to Sandy Brown, Human Resources, at
  • Kitchen Staff: Line Cooks and Prep Cooks (AM and PM shifts), some experience necessary, but will train the right person
  • Bussers: lunch and dinner service
  • Host/Hostess: AM and PM shifts, experience preferred but will train the right person
  • Housekeeping: Part Time Weekend Housekeeping
  • Servers: Breakfast, Lunch and Dinner shifts, part-time or full-time.
  • Experience preferred, but will train the right person
  • Housekeeping: Part Time Weekend Housekeeping

We seek individuals who are professional, friendly, responsible, punctual, and willing to work in a team-oriented atmosphere. We offer competitive compensation and flexible schedules for most positions. Full-time, part-time, seasonal and year-round positions are usually available. Consider joining America’s first family of hospitality.

If you’re interested in becoming part of our legendary service family, please use the form below or send your resume with a cover email to No phone calls, please.

The Wayside Inn Foundation does not discriminate on the basis of race, color, religious creed, national origin, ancestry, sex, gender identity, age, criminal record (although some positions may require CORI clearance), handicap (disability), mental illness, retaliation, sexual harassment, sexual orientation, active military personnel, and genetics.

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