Forty miles of sandy beaches, lighthouses, hiking and biking trails, history dating back to 1797, beautiful sunrises, great food, festivals, and nightlife, make the busy summer destinations of Cape Cod and the islands of Nantucket and Martha’s Vineyard great destinations for the seasonal adventurer.
Dennis Port, Massachusetts
🐄⛵ Front of the House Manager – The Sailing Cow Café (Dennis Port, MA)
Edgartown, Massachusetts
Come Live, Work, & Play on Martha's Vineyard Island in the 2026 Season
Since 1995, CoolWorks has connected adventure-seekers with job opportunities in amazing places—from national parks to ski resorts, summer camps to dude ranches. We help people trade screen time for real time—meaningful experiences that spark connection and growth. Your next great adventure is waiting. More About CoolWorks
The CoolWorks Compass newsletter offers a sampling of new jobs, along with tips and inspiration to help you chart your next adventure!