After successful stints at Ralph Lauren Polo and Abercrombie & Fitch, designer Alex Carleton opened Rogues Gallery (41 Wharf St., (207) 553-1999), a nautical-inspired clothing store in Portland. When he’s not hand-printing whale flukes on T-shirts, Carleton spends time at these nearby spots. —Meeghan Truelove

“The Portland Observatory (138 Congress St., (207) 774-5561) is my favorite structure in the city. It’s an octagonal clapboard tower built in 1807 to signal when ships arrived in port. Inside is the best antique graffiti in town—names in curlicue letters carved into the wood during the 19th century.”

“On any given night at the Space Gallery (538 Congress St., (207) 828-5600), you can catch a concert, an art opening, or an indie film.”

“I love the collection at the Portland Museum of Art (7 Congress Sq., (207) 775-6148), especially the works by American painters Winslow Homer, Rockwell Kent, and Andrew Wyeth.”

Image courtesy of Rogues Gallery. This appeared in the July/August 2011 issue.