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Pick Your Own Booth Attendant (Seasonal)

Nashoba Valley Winery, Distillery and Brewery
Bolton, MA Part Time
POSTED ON 8/6/2026
AVAILABLE BEFORE 12/3/2026

Nashoba Valley Winery | Bolton, MA

Job Details

  • Job Type: Seasonal
  • Season: September 5, 2026 – November 1, 2026
  • Pay: $15.00 per hour shared tips
  • Expected Tip Average: An additional $8–$10 per hour through a tip pool shared across the entire Winery operation.

About the Position

Nashoba Valley Winery is looking for friendly, energetic, and dependable team members to join our Pick Your Own (PYO) Team during one of our busiest and most exciting seasons of the year.

As a Pick Your Own Booth Attendant, you'll be one of the first people guests meet when they arrive for apple picking. You'll help create an exceptional guest experience by welcoming visitors, selling apple bags, providing picking instructions and orchard maps, and serving cider donuts, beverages, and other seasonal favorites.

This is a fast-paced position that requires excellent customer service, a positive attitude, and the ability to stay organized while assisting hundreds of guests throughout the day.

Schedule

Season Dates: September 5, 2026 – November 1, 2026

Required Availability

Applicants must be available to work every Saturday and Sunday during the entire season.

Weekend availability is required. Because of the short season and high guest volume, we are unable to accommodate recurring weekend absences.

Shift Times

  • Saturday: 10:00 AM – 5:30 PM
  • Sunday: 10:00 AM – 4:30 PM

Responsibilities

  • Welcome guests arriving for Pick Your Own apples.
  • Sell Pick Your Own apple bags and explain the picking process.
  • Provide guests with orchard maps and direct them to the appropriate picking locations.
  • Answer questions about apple varieties, orchard rules, and farm activities.
  • Sell fresh cider donuts, beverages, and other grab-and-go items.
  • Prepare and serve alcoholic and non-alcoholic beverages.
  • Verify IDs and follow all Massachusetts alcohol service laws and company policies.
  • Process transactions accurately using our point-of-sale system.
  • Keep the booth clean, organized, stocked, and guest-ready throughout the day.
  • Restock merchandise, beverages, and food items as needed.
  • Work collaboratively with orchard, retail, and hospitality staff to provide an outstanding guest experience.
  • Maintain a friendly, welcoming attitude while working in a fast-paced environment.

Qualifications

  • Must be at least 21 years old.
  • Previous customer service, retail, food service, or hospitality experience is preferred but not required.
  • Comfortable working outdoors in various weather conditions.
  • Strong communication and interpersonal skills.
  • Ability to multitask while maintaining accuracy and professionalism.
  • Reliable, punctual, and team-oriented.
  • Ability to stand for extended periods and lift up to 30 pounds.
  • Comfortable serving alcoholic beverages and checking IDs.

Compensation & Benefits

  • $15.00 per hour plus shared tips.
  • Tips are pooled across the entire Pick Your Own operation and typically average an additional $8–$10 per hour, depending on business levels.
  • Employee discount on food, beverages, wine, cider, beer, spirits, and retail merchandise.
  • Work in a fun, fast-paced outdoor environment during New England's peak fall season.
  • Join a welcoming team while helping create memorable experiences for thousands of guests.

Work Location

Nashoba Valley Winery
100 Wattaquadock Hill Road
Bolton, MA 01740

Work Location: In person

Pay: $15.00 per hour

Benefits:

  • Employee discount

Work Location: In person

Salary : $8 - $10

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