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Weekend Pilot Jobs in Connecticut (NOW HIRING)

Navstar

Production / Training Pilot Jobs

Stratford, CT · On-site

Pilots production aircraft during engineering and production acceptance. Pilots aircraft or acts as instructor pilot for training customer pilots and aircrew during syllabus training flights; may ...

Kombo

Commercial Airline Pilot

Stamford, CT · On-site

As a Commercial Airline Pilot, you will be responsible for safely operating aircraft, ensuring passenger safety, and maintaining the highest standards of professionalism and operational excellence.

Kombo

Commercial Airline Pilot

Stamford, CT · On-site

As a Commercial Airline Pilot, you will be responsible for safely operating aircraft, ensuring passenger safety, and maintaining the highest standards of professionalism and operational excellence.

PenBay Media LLC

Remote Pilot Operator

Windsor Locks, CT · On-site +1

$21.98/hr

The Remote Pilot Operator (RPO) operates a combination of Cathode Ray Tube (CRT)/keyboard/Voice Communication System (VCS) to simulate the actions and communication of pilots and remote ATC ...

American Cruise Lines

River Pilot

Guilford, CT · On-site

$111 - $185/hr

American Cruise Lines seeks experienced Nav Mate Pilots to lead our U.S. - flag fleet. American Cruise Lines cruise along inland and coastal waterways, including the East Coast, Alaska, Pacific ...

Imh

Rotor Wing Pilot in Command

Hartford, CT · On-site

$46.24 - $72.80/hr

As an Air Ambulance Pilot, you are the critical link in delivering rapid, life-saving transportation for patients in need. Your expertise ensures the safety of the medical team and patients during ...

NetJets & EJM

Pilot in Command Global 6000

Stratford, CT · On-site

$250K - $300K/yr

This is a 2-pilot account supported by a dedicated Maintenance Technician flying approximately 260 hours annually, part 91 and 135. Based on your qualifications and interest, there may be an ...

Pilot Company

Travel Center Assistant Manager

Milford, CT · On-site

$69K - $84K/yr

Company Description Pilot Company is an industry-leading network of travel centers with more than ... Furthermore, you must be able to work a flexible schedule of nights, days, weekends and holidays.

Pilot Company

Travel Center Assistant Manager

Milford, CT · On-site

$69K - $84K/yr

Company Description Pilot Company is an industry-leading network of travel centers with more than ... Furthermore, you must be able to work a flexible schedule of nights, days, weekends and holidays.

Clay Lacy Aviation

$330K - $390K/yr

This is a 3 pilot account. The opportunity features anupgraded compensation plan, fully paid medical/healthcare, and a matching 401(k) plan. * Position : Captain * Aircraft : Gulfstream G600

Pilot Flying J

Travel Center Assistant Manager

Milford, CT · On-site

$69K - $84K/yr

Company Description Pilot Company is an industry-leading network of travel centers with more than ... Furthermore, you must be able to work a flexible schedule of nights, days, weekends and holidays.

Pilot Company

Cashier

Milford, CT · On-site

$16.94 - $20.68/hr

Pilot Company offers a dynamic environment where no two days are the same. Team members have the ... Ability to work a flexible schedule of nights, days, weekends, and holidays Additional Information

Pilot Company

Deli Production Team Member

Milford, CT · On-site

$16.94 - $22.33/hr

Pilot Company offers a dynamic environment where no two days are the same. Team members have the ... Ability to work a flexible schedule of nights, days, weekends, and holidays Preferred ...

Pilot Company

Cashier

Milford, CT

$16.94 - $20.68/hr

Pilot Company offers a dynamic environment where no two days are the same. Team members have the ... Ability to work a flexible schedule of nights, days, weekends, and holidays Additional Information

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All JobsPilot JobsWeekend Pilot JobsWeekend Pilot Jobs in Connecticut

Weekend Pilot information

See Connecticut salary details

$47.1K

$124.5K

$191.2K

How much do weekend pilot jobs pay per year?

As of Sep 6, 2026, the average yearly pay for weekend pilot in Connecticut is $124,539.00, according to ZipRecruiter salary data. Most workers in this role earn between $95,100.00 and $147,400.00 per year, depending on experience, location, and employer.

What is a weekend pilot?

Weekend Pilots are licensed aviators who typically fly aircraft on weekends, often working part-time or on a flexible schedule. They may fly for private individuals, charter companies, or recreational purposes, and sometimes assist with sightseeing tours, aerial photography, or transporting passengers and cargo. Weekend Pilots must meet the same licensing and training requirements as full-time pilots, but their flying hours are usually limited to Saturdays and Sundays. This role is ideal for experienced pilots seeking a part-time commitment or aviation enthusiasts looking to maintain their skills.

What does a weekend pilot do?

A weekend pilot has similar job duties as pilots who work during the week. The primary difference is they work over the weekend. Your specific job duties vary, depending on the kind of plane you fly and if you are a commercial or cargo pilot. General responsibilities for commercial pilots include studying weather reports and schedules, evaluating the fuel load requirements, preparing the flight plan, ensuring safety for passengers, and checking all hardware for plane safety and navigation equipment. Cargo pilots discuss the goods being transported with the shipping company and clarify where the load needs to be delivered. They ensure the shipment has been loaded completely and is adequately secured, and delivers it on time when possible. Weekend pilots work Saturdays and Sundays, but may also have shifts on Fridays or Mondays.

What are the key skills and qualifications needed to thrive as a weekend pilot, and why are they important?

To thrive as a Weekend Pilot, you generally need a valid pilot’s license (such as a Private Pilot Certificate), strong knowledge of aviation regulations, and proficient flight skills. Familiarity with navigation systems, aircraft instrumentation, and weather assessment tools is crucial, and sometimes an FAA medical certificate or additional ratings may be required. Exceptional decision-making, communication, and situational awareness help pilots adapt to changing conditions and ensure passenger safety. These skills and qualifications are essential for safe, compliant, and effective operation of flights, especially when flying on tight schedules or in variable weekend conditions.

What are some common challenges weekend pilots face when balancing flying with other commitments?

Weekend pilots often juggle their flying schedules with full-time jobs or family responsibilities, which can make it difficult to log consistent flight hours and maintain proficiency. Weather delays, aircraft availability, and airspace congestion are typical challenges that can disrupt planned flights. To stay current and confident, many weekend pilots join flying clubs, coordinate with other pilots for shared rentals, and make use of online scheduling tools to maximize their time in the air while managing other commitments.

What is the difference between Weekend Pilot vs Part-Time Flight Attendant?

AspectWeekend PilotPart-Time Flight Attendant
Required CertificationsCommercial Pilot License (CPL), FAA medical certificateFlight Attendant Certification, CPR/First Aid
Work EnvironmentAircraft cockpit, airports, flight operationsPassenger cabin, airports, in-flight service
Employer & IndustryAirlines, charter companiesAirlines, private jet services
Common Search & ComparisonWeekend Pilot vs Part-Time Flight Attendant

Weekend Pilots typically hold commercial pilot licenses and operate aircraft, focusing on flying duties during weekends. Part-Time Flight Attendants primarily provide passenger service and safety onboard, often working part-time hours. Both roles are essential in the aviation industry but differ in responsibilities, certifications, and work environment.

Do weekend pilots work on weekends?

Weekend pilots typically work on weekends as part of their scheduled shifts, which often include Saturday and Sunday flying hours. Their schedules depend on the employer, flight routes, and operational needs, and they may need to be flexible with their availability. Certification and safety regulations also influence their work hours and scheduling.
More about Weekend Pilot jobs

What are the most commonly searched types of Pilot jobs in Connecticut?

The most popular types of Pilot jobs in Connecticut are:

What are popular job titles related to Weekend Pilot jobs in Connecticut?

For Weekend Pilot jobs in Connecticut, the most frequently searched job titles are:

What job categories do people searching Weekend Pilot jobs in Connecticut look for?

The top searched job categories for Weekend Pilot jobs in Connecticut are:

What cities in Connecticut are hiring for Weekend Pilot jobs?

Cities in Connecticut with the most Weekend Pilot job openings:

Weekend Pilot jobs near you
Infographic showing various Weekend Pilot job openings in Connecticut as of August 2026, with employment types broken down into 1% As Needed, 67% Full Time, 28% Part Time, 3% Contract, and 1% Nights. Highlights an 94% Physical, 1% Hybrid, and 5% Remote job distribution, with an average salary of $124,539 per year, or $59.9 per hour.

Jet Pilot

Massachusetts Mutual Life Insurance Company (MassMutual)

Windsor, CT • On-site

$244K - $320K/yr

Full-time

Posted 9 days ago

MassMutual rating

7.8

Company rating: 7.8 out of 10

Based on 37 frontline employees who took The Breakroom Quiz

197th of 315 rated insurance

Job description

Jet Pilot
Aviation Department
Full-time
Bradley International Airport, Windsor Locks, CT
The Opportunity
A key component to the Aviation Department, the Jet Pilot ensures safe, reliable, and flexible transportation for all passengers traveling on corporate aircraft. The Jet Pilot coordinates extensively with passengers, other flight crewmembers, flight scheduling and maintenance management. The position is responsible for the safe and efficient conduct of all assigned flights with scheduled trips with good judgment always prevailing.
The Team
An integral part of the MassMutual Aviation Department, the Jet Pilot Group handles operations domestically and international. We are a department recognized by our corporate stakeholders, principals, customers, and business partners as "The Solution" for complex transportation requirements.
The Impact:
  • Provides excellent customer service to passengers
  • Validates trip details prior to departure
  • Complies with schedules and other directives governing the aircraft's operation
  • Ensures that all flight-planning requirements have been met
  • Operates the aircraft per standard operating procedures and within aircraft limitations
  • Participates in the Safety Management System
  • Maintains currency and proficiency in assigned Flight Department aircraft
  • Assumes any duties delegated by the Chief Pilot and/or Assistant Chief Pilot

The Minimum Qualifications
  • High School Diploma or GED
  • 7+ years experience of corporate aviation, charted operations/121, or military aviation VIP experience
  • Holds an Airline Transport Pilot Certificate with Multi-Engine Rating (fixed wing)
  • Holds a First Class FAA Medical Certificate
  • 3000 hours flight time with 2000 hours as pilot in command
  • Resides within 1.5 hours of the primary job location (Windsor Locks, CT)

The Ideal Qualifications
  • Experience with Falcon 2000LXS and/or Falcon 8X
  • Experience operating Internationally (to include Oceanic operations)
  • Ability to work a non-standard schedule to include nights, weekends, and standby days as determined by the flight schedule
  • Experience working within a corporate flight department
  • Excellent verbal and written communication skills
  • Bachelor Degree
  • Must be eligible to work in the United States without sponsorship now or the in the future

What You Can Expect at MassMutual
MassMutual offers the opportunity to do meaningful work within a purpose-driven organization that values long-term impact over short-term outcomes. In this role, you can expect:
Clear areas of ownership and accountability, with work that connects directly to company and customer outcomes
A collaborative environment where perspectives are welcomed
Access to learning, development, and internal networks that support continuous growth and skill-building over time
Employee-led communities and forums that foster connection, learning, and inclusion across the organization
A culture grounded in integrity, responsibility, and stewardship-supported by a company with a strong legacy and a future-focused mindset
"Employment is contingent upon successfully passing a drug screening, RMV check and background check."
#LI-EG1
Salary Range:
$244,000-$320,100
At MassMutual, we focus on ensuring fair equitable pay, by providing competitive salaries, along with incentive and bonus opportunities for all employees. Your total compensation package includes either a bonus target or in a sales-focused role a Variable Incentive Compensation component.
Why Join Us.
We've been around since 1851. During our history, we've learned a few things about making sure our customers are our top priority. In order to meet and exceed their expectations, we must have the best people providing the best thinking, products and services. To accomplish this, we celebrate an inclusive, vibrant and diverse culture that encourages growth, openness and opportunities for everyone. A career with MassMutual means you will be part of a strong, stable and ethical business with industry leading pay and benefits. And your voice will always be heard.
We help people secure their future and protect the ones they love. As a company owned by our policyowners, we are defined by mutuality and our vision to put customers first. It's more than our company structure - it's our way of life. We are a company of people protecting people. Our company exists because people are willing to share risk and resources, and rely on each other when it counts. At MassMutual, we Live Mutual.
MassMutual is an equal employment opportunity employer. We welcome all persons to apply.
If you need an accommodation to complete the application process, please contact us and share the specifics of the assistance you need.
At MassMutual, we focus on ensuring fair, equitable pay by providing competitive salaries, along with incentive and bonus opportunities for all employees. Your total compensation package includes either a bonus target or in a sales-focused role a Variable Incentive Compensation component. For more information about our extensive benefits offerings please check out our Total Rewards at a Glance.

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