A LONG AND WINDING ROAD | Drawing on the songs of Joni Mitchell, Jimmy Webb, Paul Simon, Carole King, James Taylor, Bob Dylan, John Lennon, Paul McCartney, and Laura Nyro, Grammy winner Maureen McGovern reconnects with her boomer roots in this show based, we imagine, on her 2008 album of the same name. Philip Himberg directs. | Boston Center for the Arts, Virginia Wimberly Theatre, 539 Tremont St, Boston | 617.266.0800 | October 9–November 15 | Curtain 7:30 pm Tues [no October 27] | 2 pm [October 28, November 4] + 7:30 pm [7 pm October 14] Wed | 7:30 pm Thurs | 8 pm Fri | 2 pm [no October 31] + 8 pm Sat | 2 pm [no October 11 or November 8] + 7 pm [October 11; November 1, 8] Sun | $20-$60
OLEANNA | Contemporary Theatre of Boston takes on David Mamet’s 1992 play — which premiered right here in Cambridge — about a university student who after seeking personal instruction from a professor accuses him of sexual harassment and ruins his chances of getting tenure. So, who did what? Judith Kallora and Allan Mayo star; Chris Cavalier directs. | Boston Center for the Arts, Calderwood Pavilion, 527 Tremont St, Boston | 617.933.8600 | October 8-17 | Curtain 7:30 pm Wed-Thurs | 8 pm Fri-Sat | 4 pm Sun | $22.50-$25
THE SEAFARER | Charles Towers directs this second area production (the first came from SpeakEasy Stage last November) of Conor McPherson’s 2008-Tony-nominated play set in a moribund suburb of Dublin on Christmas Eve. Dickens it’s not — McPherson’s spirits of Christmas Past, Present, and probably Future come in a bottle. But McPherson’s claim that this grimly humorous work is his most optimistic play yet is not without credence. Sharky is a multiple loser who’s returned from his latest misadventure to care for his recently blinded brother Richard, who sets up a late-night poker game that includes a mysterious interloper with some very high stakes in mind. This suave stranger is Satan, and Sharky is playing for his very soul. With David Adkins as Sharky and Gordon Joseph Weiss as Richard. | Merrimack Repertory Theatre, 50 East Merrimack St, Lowell | 978.654.4MRT | October 15–November 8 | Curtain 2 pm [October 21] + 7:30 pm Wed | 7:30 pm Thurs | 8 pm Fri | 4 pm [no October 17] + 8 pm Sat | 2 + 7 pm [no evening November 8] Sun | $26-$56
SHOOTING STAR | Real-life couple Kurt Rhoads and Nance Williamson, who starred in Trinity Rep productions in the early ’90s, return to Providence for Steven Dietz’s romantic comedy about ex-lovers who run into each 20 years later in a snowbound Midwest airport. Fred Sullivan Jr. directs. | Trinity Repertory Company, 201 Washington St, Providence, Rhode Island | 401.351.4242 | October 16–November 22 | Curtain 7:30 pm Tues-Fri [with a 2 pm matinee October 28] | 2 pm [October 24; November 7, 21] + 7:30 pm Sat | 2 pm [no October 18] + 7:30 pm Sun | $20-$65
