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Server Winter Jobs in Boston, MA (NOW HIRING)

Karen Clark & Company

Software Engineer

Boston, MA · On-site

$85K - $110K/yr

... storms, floods, earthquakes, winter storms, and wildfires in over 50 countries. For more ... Experience working with large and complex databases (MS SQL Server) * Excellent problem solving ...

Karen Clark & Company

Software Engineer

Boston, MA · On-site

$85K - $110K/yr

... storms, floods, earthquakes, winter storms, and wildfires in over 50 countries. For more ... Experience working with large and complex databases (MS SQL Server) * Excellent problem solving ...

Karen Clark & Company

Software Engineer

Boston, MA

$85K - $110K/yr

... storms, floods, earthquakes, winter storms, and wildfires in over 50 countries. For more ... Experience working with large and complex databases (MS SQL Server) * Excellent problem solving ...

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All JobsServer Winter JobsServer Winter Jobs in Boston, MA

Server Winter information

See Boston, MA salary details

$6

$16

$33

How much do server winter jobs pay per hour?

As of Aug 19, 2026, the average hourly pay for server winter in Boston, MA is $16.61, according to ZipRecruiter salary data. Most workers in this role earn between $11.25 and $18.80 per hour, depending on experience, location, and employer.

What is a server winter?

A Server Winter is a hospitality worker who serves food and beverages to guests, specifically during the winter season at resorts, lodges, or restaurants in winter destinations. Their responsibilities include taking orders, delivering meals, ensuring guest satisfaction, and sometimes handling payments. Server Winters often work in ski resorts, mountain lodges, or other venues that experience peak business during the colder months. This seasonal role requires excellent customer service skills and the ability to work in fast-paced environments.

What are the key skills and qualifications needed to thrive as a server in a winter seasonal setting?

To thrive as a Server in a winter setting, you need strong customer service skills, basic food and beverage knowledge, and often previous experience in hospitality. Familiarity with point-of-sale (POS) systems and, in some cases, alcohol serving certifications are typically required. Outstanding interpersonal skills, teamwork, and the ability to remain calm under pressure help servers deliver exceptional guest experiences during busy peak seasons. These abilities are crucial for maintaining efficient service and positive client relations in high-demand winter resort or restaurant environments.

What are some unique challenges servers face during the winter season at resorts or ski lodges?

Servers working in winter resort settings often experience high guest volumes during peak holiday times, which can lead to fast-paced shifts and increased pressure to deliver excellent service. Additionally, navigating icy or snowy conditions—both outside and sometimes inside—can make transporting food and drinks more challenging. Teamwork is crucial, as servers must coordinate with kitchen staff and fellow servers to manage large groups and special events typical of the winter season. Flexibility with scheduling is also important, as demand can fluctuate with weather and holiday bookings.

What is the difference between Server Winter vs Server Summer?

AspectServer WinterServer Summer
CertificationsFood Handler Permit, Alcohol Service CertificationFood Handler Permit, Alcohol Service Certification
Work EnvironmentIndoor, colder months, slower seasonIndoor, warmer months, peak season
Industry UsageOff-season staffing, seasonal rolesPeak season staffing, high customer volume

Server Winter and Server Summer roles share similar certifications and work environments but differ mainly in seasonal demand. Server Winter typically involves off-season work with lower customer volume, while Server Summer is associated with peak season, higher tips, and busier shifts. Understanding these differences helps job seekers choose roles aligned with their seasonal availability and career goals.

What are popular job titles related to Server Winter jobs in Boston, MA?

For Server Winter jobs in Boston, MA, the most frequently searched job titles are:

What job categories do people searching Server Winter jobs in Boston, MA look for?

The top searched job categories for Server Winter jobs in Boston, MA are:

Server Winter jobs near you
Infographic showing various Server Winter job openings in Boston, MA as of August 2026, with employment types broken down into 74% Full Time, 20% Part Time, and 6% Contract. Highlights an 93% Physical, 3% Hybrid, and 4% Remote job distribution, with an average salary of $34,556 per year, or $16.6 per hour.

Server Assistant

Mile Marker One Waterfront Restaurant

Gloucester, MA

Full-time

Re-posted 2 days ago

Job description

SERVER ASSISTANT / FOOD RUNNER

Do you love hospitality and the marina lifestyle? Are you looking for a role where you can play a vital part in ensuring unforgettable experiences for restaurant guests? Mile Marker One - Waterfront Dining in beautiful Gloucester, MA is looking for you! We are hiring for late April and May.

Mile Marker One is a vibrant restaurant serving breakfast, brunch, lunch, and dinner year-round, nestled on a picturesque marina. We offer diverse dining experiences, from our cozy indoor space and unique igloo dining in cooler months to our stunning outdoor Bridge Deck that opens in late spring. Our team, including servers and bartenders, is dedicated to providing exceptional service. We often feature live music with dinner, host wine tasting events, and more. As we gear up for our busy season, expanding to 7 days a week in late spring, we're seeking enthusiastic individuals to support our serving team. Mile Marker One is a fun, friendly place known for amazing scallops, oysters, seafood, and delicious dishes from burgers to lobster rolls. We thrive in a fast-paced environment during the Summer and Fall and offer unique culinary events in the Winter and Spring. We also host corporate events, rehearsal dinners, and private dining in our restaurant and event space. Plus, we're conveniently attached to a hotel with an indoor heated pool and jacuzzi.

This is a seasonal position.

Server Assistant/Food Runner Location: Gloucester, MA, 01930 Skills: Passion for hospitality, strong teamwork skills, attention to detail, ability to hustle. Position Summary: As a Server Assistant/Food Runner at Mile Marker One, you will be a crucial support member of our service team, ensuring the smooth and efficient delivery of food and beverages to our guests. You will work closely with servers to enhance the guest experience by delivering orders promptly, maintaining table cleanliness, and assisting with various tasks to ensure seamless service.

Responsibilities:

  • Food and Beverage Delivery: Retrieve food and beverage orders from the kitchen and bar and deliver them accurately and efficiently to guest tables.
  • Table Awareness: Know table numbers and seat positions to ensure correct delivery.
  • Pre-Bussing: Clear tables of finished plates, glassware, and debris promptly and efficiently throughout the dining experience.
  • Table Maintenance: Assist servers in maintaining table cleanliness, refilling water glasses, and ensuring guests have everything they need.
  • Running Food: Prioritize and expedite the delivery of food orders to ensure optimal food quality and guest satisfaction.
  • Assisting Servers: Support servers with various tasks, such as setting tables, stocking service stations, and running errands as needed.
  • Communication: Communicate effectively with servers, kitchen staff, and management regarding order readiness and any potential issues.
  • Restaurant Knowledge: Develop a basic understanding of menu items to answer simple guest questions and identify dishes.
  • Safety and Sanitation: Follow all safety and sanitation procedures to maintain a clean and healthy environment for guests and staff.
  • Side Work: Assist with assigned side work duties, including stocking stations, preparing condiments, and ensuring the overall cleanliness of service areas.
  • Teamwork: Work collaboratively with all team members to provide exceptional guest service.

Qualifications:

  • A genuine passion for hospitality and a desire to learn about the restaurant industry.
  • Strong teamwork and collaboration skills.
  • Excellent communication and interpersonal skills with a positive and friendly attitude.
  • Ability to multitask, prioritize, and work efficiently in a fast-paced environment.
  • Attention to detail and a sense of urgency.
  • Ability to follow instructions carefully.
  • Ability to work a flexible schedule, including evenings, weekends, and holidays as needed.

Apply