(Enlarge) Laura Rocklyn and Dave Gamble get drawn into the mistaken identities of "Twelfth Night," opening this week at Chesapeake Shakespeare Company.

When Jenny Leopold set out to direct her first summer production for the Chesapeake Shakespeare Company, she acknowledged a fair amount of trepidation. The troupe's seasonal outdoor shows are not only big, demanding affairs, they are dependent on good weather.

Yet, in spite of the rainier-than-usual last couple of months, Leopold's theatrical adventure beneath the Bard's "brave, o'erhanging firmament" turned out, well, just great, according to the director.

The result will be unveiled for all this Friday, June 26, when the classical drama troupe opens Leopold's staging of the Shakespearean comedy "Twelfth Night."

"The upside of it being such a big production is that I've had a lot of help," explains the longtime Columbia resident.

While the company sometimes experiments with bare-bones production values during its winter indoor stagings at the Howard County Center for the Arts, no expense is spared for its lavish outdoor shows.

"We have a huge design team," notes Leopold. "Not only do I have a set designer and technical designer, I've got a musical director working with me. I've also got Christopher Niebling doing our fight choreography."

On top of all that, Leopold's lead actress, Jenny Crooks, is serving as Leopold's assistant director and "movement coordinator." That means when she's not directly on stage in the lead role of Viola or giving personal attention to other actors, Crooks is off choreographing the play's critical dance scenes.

"Twelfth Night" is being mounted in the Chesapeake Shakespeare Company's "Shakespeare in the Ruins" series, and is part of this year's "double header" (with "Cyrano de Bergerac") on the grounds of the abandoned Patapsco Female Institute.

For Leopold, directing this play is something of an artistic coup. Although she once directed a "workshop production" of the bard's "Love's Labor's Lost" for the company, this is her first turn at the helm of a major Chesapeake production.

The play definitely requires directorial experience, since it's a fast-paced farce, full of mistaken identities and doubles entendre. It follows a shipwrecked woman, Viola, who loses contact with her twin brother and must disguise herself as a boy to work in the court of Duke Orsino. Orsino is distracted with his own crises after being thwarted by the Lady Olivia, who, believing Viola is a man, falls in love at first glance.

A lot of the comedy, though, revolves around Olivia's buffoonish head steward, Malvolio, a pretentious know-nothing who believes Olivia is in love with him.

Since the play touches on how the mores in Shakespeare's time were changing, Leopold has transplanted the play in the pre-Beatles 1960s, an era of similarly tumultuous changes, she says.

"I liked the early '60s, because we still have some of that conservative feel of the '50s, and yet there is a hint of what's to come," Leopold says. "We're not yet in the full-blown psychedelic era, but we do have a touch of that mod feel."

Leopold says she envisions Orsino's court as a workplace where the "women who work for him wear pantsuits," and the count is trying to modernize himself: "While he's certainly not a liberal, I think he's trying in some ways to take on a little more modern role in the world."

Leopold also adds that the play deals with "the nature of love, which is always relevant."

"Twelfth Night" will also boast original music. However, the music dates back to the troupe's first staging of the play, which was its first-ever production back in 2002. The songs were composed by then-company member Dan O'Brien, a Baltimore resident, and will be sung by a more familiar face this time around, Leopold explains.

"For our production, we have Steve Beall singing the songs," Leopold says. "He's another Columbia resident who has been involved in community theater for a long time."

The Chesapeake Shakespeare Company will perform "Twelfth Night" June 26-July 19 at the Patapsco Female Institute Historic Park, 3691 Sarah's Lane in Ellicott City. Performance times are Fridays-Saturdays 8 p.m. and Sundays 5 p.m.

Admission is $25 general on Fridays, $30 on Saturdays and Sundays. Admission for seniors runs $22-$27. Students under 22 are admitted for $15 and children under 18 are admitted free with a paying adult. An extended version will be staged Friday, July 17. A double-bill of "Twelfth Night" and "Cyrano de Bergerac" will be presented this Saturday, June 27. For information, go to www.chesapeakeshakespeare.com, or call 866-811-4111 or 410-313-8874 for group sales.

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