Topside Grill
50 Rogers Street, Gloucester, MA
(978) 281-1399

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The Topside Grill originally opened as the famous Schooners of Gloucester Restaurant and Topside Pub in 1987 when Dennis Silva, former chef of the Downeast Oyster House, decided that he wanted to take his passion for the restaurant business to the next level. He had been in the restaurant business his whole life growing up in Boston and Revere. His resume includes Saucier Chef at the Colonnade in Boston, night chef at the Logan Hilton, The Sheraton in Boston, The Plantation Beef Steak House, and The Pillar House in Newton.

Dennis eventually moved to Gloucester with his family in 1982 as head chef of the Downeast Oyster House and helped make the restaurant one of the most popular destinations in the eighties for anyone visiting or living in Gloucester. With the success of the Downeast, Dennis decided to take a risk and start his own restaurant and do things the way he had always dreamed of. The opportunity soon presented itself to buy the former Squire Wills restaurant in 1987(The current building you are in now). “We loved the location and the history behind the building” after some renovations, the dream of Schooners had become a reality. Dennis and his wife worked practically nonstop to make the restaurant a success over the next few years. There were a lot of great times to go along with the excellent food. With the help of an excellent staff and Dennis’ wife, brother’s in law and two son’s helping out as much as possible Schooners was the destination of choice in Gloucester throughout the nineties.

In 1994 the astonishing success of Schooners had presented itself with a new opportunity. The old Downeast Oyster House had gone out of business and the building was for sale. Dennis now had the opportunity to purchase the old restaurant which had brought him to the wonderful city of Gloucester. Dennis bought, renovated and opened the restaurant as the Windjammer in 1994 and embarked on a new restaurant adventure and in a way, coming full circle with that which brought him here in the first place. Now with two successful restaurants, Dennis and his family (his two sons taking on a greater role) continued to work very hard to continue to bring the same recipe of success to both locations.

As you may or may not know, the restaurant business is a very tough business and very demanding. And after a widely successful run, opportunity presented itself once again. In 2000, the manager of Schooners offered to buy the business from Dennis. It was a great time to begin to ease out of the business that had been so successful but consumed so much of his life. A year later a similar opportunity arose with the Windjammer. Dennis and his wife Dawn decided to retire and enjoy some of the things they missed out on while they were running the business’.

Schooners went through a couple owners and in 2007 the opportunity to purchase the business came back to him. His passion had returned. He decided to start over and re-open with the name Topside Grill. He missed the smiling faces, the happy customers, the stories, and the staff. His son Doug, who was at the time a financial advisor in Boston, wanted to get involved as well to eventually take the business over.

Doug had just started bartending and managing when the restaurants were originally sold. He continued his education at the University of Massachusetts Amherst and graduated with majors in business management, economics and marketing. He always had a passion for bartending and the restaurant business even while his professional career directed him into the world of finance. He always had a part time job bartending somewhere. His resume includes the sports bar Rafters in Amherst in college, (Leisure) casino boats, piano bars (The Studio), clubs (Avalon & Embassy) in Boston, fun spots (Fire & Ice), and upscale dinning (Excelsior Restaurant & Lounge). Doug is now acting partner and the General Manager of Topside. He also went to culinary school for his chef certification, graduating at the top of the class. He is responsible for the day to day activities of the restaurant, menu design and all staffing.  Dennis is now (Semi) retired but still comes into the restaurant regularly.  

Things in Gloucester have changed a lot through the years. Some restaurants have closed and new establishments have opened but excellent food, wonderful service and reasonable prices is the recipe that worked before, and with the help of family, and our wonderful staff the success of the restaurant will continue to work now and in the future. Thank You for joining us here at The Topside Grill. We hope you will make yourself comfortable and enjoy everything we have to offer. If you enjoy your experience here, please tell your friends and family. If not…Please tell us and we will do everything we can to improve as best we can.