From alfresco Shakespeare productions to automobile races, Connecticut’s cultural calendar is crowded between Memorial Day and Labor Day. Even the tiniest of towns have summer-fun events, many of which you can walk to. To celebrate them, we’ve chosen six lovely listings that will put you in close proximity to these pleasures and pastimes.

New Canaan Summer Stock
Every year, the Summer Theatre of New Canaan puts on impressive productions of plays including, this season, Hairspray and Charlotte’s Web. And its venue couldn’t be more charming: STONC makes its home in a state-of-the-art, open-air tent in gorgeous 300-acre Waveny Park, which was designed in 1912 by Frederick Law Olmsted, Jr., whose life’s projects ranged from the White House grounds to Yosemite National Park. Within about five miles of Waveny, this grand home is billed as “American Shingle meets English Arts & Crafts”—and it’s a happy marriage indeed. Designed and built by Wadia Associates, the home’s interiors offer such pleasures as a mahogany-paneled library, a home theater, a 3,800-bottle wine cellar and a gym and dance studio. On the 3.7-acre grounds sit a tennis court, a pool and spa, a formal rose garden (they’re not just for presidents any more!) and an expansive playground with slides, swings and climbing structures. Larry Palma and Becky Walsh of William Pitt Sotheby’s International Realty have the $10.5 million listing. 203-858-5909.

Enter Westport, Stage Left
The new Levitt Pavilion for the Arts, which is scheduled to reopen next month after an extensive building project, was designed by architect Peter Cadoux to feature a dramatic performance space with a sail-like roof and a wraparound path along the Saugatuck River. This home, just off Compo Road South, is equidistant between the Levitt Pavilion and Compo Beach. The 7,225-square-foot shingle-style manse on 1.33 acres was built to accommodate a large family in style. The exteriors feature a handsome cedar-shake roof, copper gutters, mahogany garage doors, Craftsman-style details and a commodious covered porch with a fireplace. Inside, find five bedrooms, including a luxe master suite with French doors that open onto a private balcony. Cathy Blount of the Riverside Realty Group has the $3,250,000 listing. 203-858-8710.
the bard in rowayton

The Bard in Rowayton
For an enchanted few weeks every June, the tiny town of Rowayton bustles with Bard-fanciers attending Shakespeare on the Sound at Pinkney Park. This year’s open-air production is Two Gentlemen of Verona, between June 12 and 29. A short distance down the coast in the private Pine Point Beach Association, this waterfront home designed by Bartels-Pagliaro is on the market for the first time since it was built in 2001. The 4,046-square-foot interiors have an open plan, starting with a dramatic, two-story entryway that opens onto an octagonal living room with French doors onto an elevated terrace with an outdoor fireplace. Throughout the house, there are expansive views of Long Island Sound and Farm Creek; the property also has a private dock. Nancy Dauk of Halstead Property in Darien has the $3,650,000 listing. 203-656-6501.

Cornwall’s Supporting Role
The little village of Lime Rock is famous for its summer-long schedule of automotive events with weekends celebrating everything on wheels, from antique cars (starts on August 28) to Trans-Am races around the park’s world-class track. We’ve chosen a listing in nearby—and quieter—Cornwall, as Lime Rock quite literally roars to life in season. Plus, this circa-2013 Scandinavian barn-style home is flat-out cool, with its pristine white exteriors and metal roofing, topped by a cupola. The spare aesthetic continues into the 3,516-square-foot interiors with their wide-width pine floors, soaring ceilings with crown moldings and chic kitchen with marble countertops, along with four bedrooms, three bathrooms (plus one half bathroom) and a cozy library with its own fireplace. For more information on this $1,295,000 listing, contact the William Pitt Sotheby’s International Realty office in Lakeville. 860-435-2400.

Shoreline Showstoppers
House tours benefiting local organizations are a win-win: Charities get a chance to fill their coffers, and residents get a glimpse into their town’s finest estates. The annual Shoreline House Tour for the Guilford Art Center opens doors to homes in Guilford, Branford and Madison on Saturday, June 7. If you’re house shopping, take the tour and then detour to this Branford beauty, a circa-1910 antique with Long Island Sound views. Steps from the Pine Orchard Association’s private beach, the white-clapboard home offers six bedrooms, including a master suite with two porches. It’s available for $1,175,000 by Joe Piscitelli of Coldwell Banker in Milford. 203-982-3511.

FIREWORK FUN
New London’s annual Sailfest ranks among the largest Independence Day celebrations in New England, attracting more than 300,000 people for three days of award-winning fireworks and music and boating events, held this year July 11–13. Just a couple of coves away in Groton, $2 million buys a spectacular view of the pyrotechnics, along with year-round vistas onto Long Island Sound, best enjoyed from the pool terrace pictured here. The 4,658-square-foot home also offers four bedrooms and three bathrooms (plus one half bathroom). Ellen Fox of Coldwell Banker in Mystic has the listing. 860-235-8333.