Request for Proposals (RFP)

Dickens of a Christmas Festival – Main Street Historic Chestertown

Event Planning & Coordination Services

Overview

Main Street Historic Chestertown is seeking proposals from qualified event planners or event management organizations to plan and coordinate the 2026 Dickens of a Christmas Festival, our signature annual event held in historic downtown Chestertown, Maryland. The Dickens of a Christmas Festival is a beloved, family-friendly holiday event that transforms downtown into a Victorian-era celebration featuring live entertainment, performances, vendors, themed experiences, and community engagement. This event serves as both a community celebration and a key fundraiser supporting Main Street Chestertown’s downtown revitalization efforts.

Key Dates

• RFP Issued: April 24, 2026
• Questions Due: May 8, 2026
• Proposals Due: June 5th, 2026
• Selection Notification: June 9, 2026

Organizational Background

Main Street Historic Chestertown is a designated Main Street Maryland community and an Accredited Main Street America program. The organization works to strengthen downtown Chestertown through economic vitality, promotion, design, and organizational development.

Due to a current staff transition, Main Street is seeking a qualified external partner to lead the planning and execution of this year’s Dickens of a Christmas Festival.

Event Overview

Event: Dickens of a Christmas Festival
Location: Downtown Chestertown, Maryland

Dates: December 4-5, 2026
Website (prior event reference): https://www.mainstreetchestertown.org/dickens

Event Elements Include:

• Live performances (music, theater, carolers)
• Vendor coordination (artisan, food, retail)
• Children’s activities and family programming
• Themed décor and placemaking
• Street closures and logistics coordination
• Sponsorship activations
• Volunteer coordination

Scope of Work

The selected consultant will serve as the lead event coordinator and will be responsible for planning, managing, and executing the Dickens Festival in collaboration with the Main Street Historic Chestertown Board.

Key Responsibilities:

Event Planning & Management

• Develop a comprehensive event plan and timeline
• Coordinate all event logistics (layout, staging, permits, etc.)
• Manage vendor recruitment, selection, and communication
• Coordinate entertainment and programming

Operations & Logistics

• Work with Town of Chestertown on permits, street closures, and public safety
• Coordinate with police, public works, and emergency services
• Oversee event-day operations and troubleshooting

Sponsorship & Revenue Support

• Assist with sponsorship outreach and fulfillment
• Identify opportunities to increase revenue (vendors, ticketing, experiences)

Marketing Coordination

• Collaborate with Main Street on event promotion strategy
• Coordinate with marketing vendors (if applicable)

Volunteer Coordination

• Recruit and manage volunteers
• Provide clear roles, schedules, and training

Post-Event Reporting

• Provide a summary report including attendance, financial performance, and
  recommendations

Budget

Base Budget: Approximately $15,000 for planning and coordination services

Optional Performance Incentive (Profit Sharing)
Main Street Historic Chestertown will consider proposals that include a performance-based incentive structure tied to event profitability of up to 10% of net profit above $5,000.

Proposal Requirements

Please include the following in your submission:

• Organization or individual overview and relevant experience
• Examples of similar events (especially festivals or downtown events)
• Proposed approach to planning and execution
• Timeline and work plan
• Staffing plan (who will be assigned to this project)
• Budget Narrative & Allocation - Provide a brief description of how the fixed project
  budget of $15,000 will be allocated across major tasks (e.g., planning, vendor coordination, event-day management, volunteer coordination, post-event reporting). Include estimated hours, key cost drivers, and any assumptions related to scope. Please identify any services or expenses that are not included in the $15,000 fee.
• Optional performance incentive proposal (if applicable)
• References (2–3 preferred)

Evaluation Criteria

Proposals will be evaluated based on:

• Relevant experience with similar events
• Demonstrated ability to manage complex, public-facing events
• Creativity and approach to enhancing the festival
• Understanding of downtown/community-based events
• Cost and value
• Ability to work collaboratively with a volunteer board

Timeline

• RFP Issued: April 24, 2026
• Questions Due: May 8, 2026
• Proposals Due: May 22, 2026
• Selection Notification: June 9, 2026

Questions & Clarifications

All questions related to this RFP should be submitted via email to:
director@mainstreetchestertown.org by May 8, 2026.

Responses to questions may be shared with all prospective proposers to ensure fairness and transparency. Questions received after the due date will not be answered.

Submission Instructions

Proposals should be submitted electronically to: director@mainstreetchestertown.org on or before June 5th, 2026.

Subject line: Dickens Festival Event Planning Proposal

Proposals received after the due date will not be considered.

Additional Information

Main Street Historic Chestertown reserves the right to:

• Accept or reject any proposal
• Negotiate scope and pricing
• Request additional information or interviews