Specialties
On the Rocks and Road is a women-owned mobile bartending company based in Massachusetts, bringing exceptional bar service to weddings, private parties, corporate events, and celebrations of all kinds. We provide customizable packages designed to fit every budget and vision, from simple bartender-only service to full bar setups with signature cocktails, hydration stations, and elegant upgrades.
All packages include essentials like coolers, linens, a curated shopping list, liability insurance, and pre-event consultations to make planning stress-free. As a dry-hire service, you supply the alcohol and we take care of the rest offering a more affordable, flexible alternative to traditional venue bar services.
Our experienced, bilingual team delivers not just drinks, but an elevated experience that helps create unforgettable memories. Every occasion, any location, On the Rocks and Road is ready to raise the bar for your event.
History
Established in 2025.
On the Rocks and Road was founded by Jackie Buchwald & Cindy Matias to bring fun, personalized, and professional bar experiences to weddings, parties, corporate events, and celebrations of all kinds. As a small, women-owned local business, we treat every event as if it were our own—creating moments that are seamless, memorable, and uniquely tailored to each client. With years in catering, from bartending to managing large weddings, we built a service that’s more than just drinks. Jackie’s background in floral design inspires her eye for detail and specialty bar displays that elevate décor, while Cindy’s bilingual services help us connect with a wide range of guests. Together, we love crafting cocktails, meeting new people, and creating celebrations that feel effortless and elevated.
Meet the Business Owner: Jackie and Cindy B.
Hi there! We’re Jackie & Cindy, the duo behind On the Rocks and Road. We started this business because we truly love seeing people come together to celebrate, and nothing makes us happier than helping those moments feel effortless and special. For us, bartending isn’t just about pouring drinks. It’s about creating an experience that adds joy, style, and connection to your event. We’re passionate about making your guests feel welcome, crafting cocktails they’ll remember, and bringing a fun, professional energy to your celebration.