Tucked away amidst a cluster of cottages on historic Rocky Neck in Gloucester sits an iconic gem called the Rudder. It’s tough to find, but an exciting discovery once you do. The restaurant sits in the middle of America’s oldest continuously working art colony, a place that was a haven for famous artists like Edward Hopper, Milton Avery, Nell Blaine, and Winslow Homer; even writers Louisa May Alcott and Rudyard Kipling spent time there.
Established in 1957 by the vivacious Evie Parsons, the Rudder has had a loyal following for decades. Now, with a renovation completed in 2010, the waterfront deck overlooking Smith Cove—guests can actually dock their boats right by the door—seats guests comfortably through rain or shine. The view that inspired decades of painters is as big of a draw as is the seafood, with sailboats and sunsets providing the backdrop for a lively evening.
Known for spectacularly fresh lobsters from Captain Joe and Sons, the Rudder also serves up quintessential summertime cocktails. Once such sipper has been a staple on the menu for 10 years and is what bartender and Rudder veteran Tony Wright says they are known for—the Ruby Red Martini. Its recipe has evolved between former staff and current bartender Laurie Logrande. It fuses grapefruit-flavored vodka and tart grapefruit juice with a touch of sweet orange liqueur. The addition of a dry, sparkling Prosecco balances the cocktail and adds a touch of effervescence. And who doesn’t love a sugared rim? The Rudder is open seasonally and is always busy. Plan your visit well in advance, especially if you’ll be arriving by boat. rudderrestaurant.com. —Brandy Rand
Ruby Red Martini: Makes one serving
2 parts Absolut Ruby Red Vodka
1 part orange liqueur (Patron Citronge or Cointreau)
1 part ruby red grapefruit juice
Prosecco to top
Shake all ingredients vigorously in a shaker filled with ice. Strain into a chilled martini glass rimmed with sugar. Top with a float of Prosecco and garnish with a wedge of red grapefruit.