Before she became an icon of American cinema—winning a record four Academy Awards for her film performances—Katharine Hepburn was a performer at a small Connecticut theater in Ivoryton. And she wasn’t alone: The Ivoryton Playhouse has welcomed the likes of Marlon Brando, Betty Grable, Mae West, Gloria Vanderbilt, Groucho Marx and Carol Channing to its stage throughout the years. Originally built in 1911 as a rec hall for factory employees of Comstock, Cheney & Co.—the ivory business that inspired the name of the town and at one time supplied Steinway with its piano keys—the 280-seat theater was later run by former Columbia Pictures director Milton Stiefel, who brought with him some serious starpower and Hollywood interest. Paramount even made the theater the lead in its own short film before the building was sold to a nonprofit foundation interested in preserving its place in the arts community.

While its current actors have yet to earn their stars on the Hollywood Walk of Fame, the theater is still making history. It kicked off its summer season with the U.S. premiere of Calendar Girls, the popular U.K. play adapted from the film of the same name, and followed it up with performances of South Pacific and Memphis. Little Shop of Horrors runs from Sept. 23 to Oct. 11, and Liberace! opens Oct. 28, proving that the picturesque village can still glam it up—and make a fun destination for a weekend getaway, only two hours from Boston.

Before a show, you can fill up on gourmet eats just down the road at the Oak Room. The restaurant is part of the Copper Beech Inn, the former residence of ivory business heir Archibald Welsh Comstock, which offers rooms in the historic main house and back carriage house as well as suites in the more modern Comstock house expansion. The inn also currently offers a Curtain Call package in partnership with the playhouse for those seeking a stay that includes dinner and a show.

Oak Room chef de cuisine Carlos Cassar’s menu can be enjoyed inside by the cozy fireplace and copper-topped bar or outside on a porch overlooking gardens and fountains. Start with an appetizer of foie gras on toast with a quince reduction and fruit chutney, and follow it with goat cheese and beet ravioli topped with toasted pignoli nuts and a basilicum sherry cream. The apple almond galette with salted caramel gelato is the perfect way to end the meal on a sweet note. As for drinks, cocktails include the Cucumber Coupe of gin, fresh cucumber and lemon, and a salt-and-pepper rim, and the Mango Mojito with rum and fresh mint. It’s the wine list at the Oak Room, however, that has repeatedly received praise, including multiple Awards of Excellence from Wine Spectator in recognition of its 2,500-bottle cellar. And did we mention the two-page Scotch menu? Better not—you have a show to catch, after all.

Thankfully, breakfast the next morning will cure you of any overzealous cask curiosity from the night before. Nibble flaky pastries and preserves while you peruse the menu of dishes like lemon ricotta hotcakes with fresh fruit and Vermont maple syrup or the Jardin du Martin breakfast of two poached eggs with hollandaise, asparagus and roasted tomatoes atop English muffins, with a side of potato rosti. Or keep things light with a granola dish of toasted oats, pumpkin seeds, cranberries, raisins and blueberry compote served with your choice of  honey yogurt or milk.

Whatever you order, save room for a mid-afternoon dessert as you head into the heart of the village of Essex, which together with the villages of Ivoryton and Centerbrook composes the town of Essex—a frequent entrant on lists celebrating the best small towns in America. Reason enough for inclusion is the Truffle Shots shop, where a mother-daughter team offers shot glasses full of non-alcoholic ganaches in 20 varieties; try dark chocolate mixed with flavors like fig balsamic, chipotle cinnamon, bourbon vanilla, mint or caramel. Walk it off by wandering Main Street, a road painted with a red-white-and-blue stripe that’s framed by white picket fences, gardens of hydrangeas and historic homes, a place where antique cars seem more at home than their modern counterparts and the vibe hasn’t changed much since Hepburn’s heyday.

Traveler’s Check     

-During the two-hour drive to Ivoryton, stop in Mystic, Connecticut, for a chance to stretch your legs and enjoy lunch at the Oyster Club’s outdoor Treehouse deck, followed by a cone at Mystic Drawbridge Ice Cream, which has been serving homemade treats in the same spot since the 1800s.

The Copper Beech Inn 46 Main St., Essex (860-767-0330) copperbeechinn.com

Ivoryton Playhouse 103 Main St., Essex (860-767-7318) ivorytonplayhouse.org

Mystic Drawbridge Ice Cream 2 W. Main St., Mystic (860-572-7978) mysticdrawbridgeicecream.com

The Treehouse at the Oyster Club Restaurant and Bar 13 Water St., Mystic (860-415-9266) oysterclubct.com

Truffle Shots 1 North Main St., Essex (860-581-8351) truffleshots.com