An evening under the summer sky watching a play or concert – it’s one of the pleasures of the season. It might be highbrow Shakespeare on the Sound in Rowayton, family fun like Pippin at The Summer Theater of New Canaan, or any one of the entertaining musical acts at Westport’s Levitt Pavilion.

A pre-performance picnic adds to the fun, extends the evening, and might even get you a better seat. At venues where there’s unreserved lawn seating, an early arrival earns a spot down front.  Dining al fresco enjoyably fills the extra time.

Picnics can be simple or elaborate. A few boxes of takeout food can fill the bill, but some like to go all out.  Tanglewood, in the Berkshires, is famous for elaborate picnics complete with table cloths and silver candelabra. Whatever your style, the food seems to taste better outdoors.

At Shakespeare on the Sound, the company takes over Pinckney Park from June 20 to July 7 (tickets $25). Seating on the sloping hillside is first come first served, so picnics are popular. The organization has made easy arrangements with lots of local food sources.

Palmer’s Market, named Best of the Gold Coast by Moffly Media for Gourmet Grocery To-Go, offers a menu of delicious sandwiches or party platters to be ordered in advance. The Palmers Veggie Van drops by the park at 6:00 for convenient delivery of pre-ordered picnics.

Sandwiches like The Gardener – tomato, hand-pulled mozzarella, and basil pine nut aioli on focaccia; or The Meat Eater – filet mignon, horseradish sauce, fried shallots and arugula on a brioche roll. They all come with a side of orzo and grilled vegetables, their famous house-made potato chips, and a freshly baked chocolate chip cookie for $16.50.

Feeding a crowd?  Palmers has platters of tapas, crostini, mezze, or picada to feed a crowd of four to six for $48.  Bring your own drinks or pick up some wine or cold beer at the nearby Rowayton Wine Shop.

Across Rowayton Avenue from the wine shop, the Rowayton Market is the source of salads, snacks, or even sushi along with some sweets and drinks.  Spread your blanket and chairs, then take the short walk to the market for picnic supplies.  They’re open till 8:00.

Charly Sahlia and his wife have been supporters of Shakespeare on the Sound for years. As owners of the popular Upper Crust Bakery at 980 Post Road in Darien, they’ve set up some special picnic packages and stay open till 5:00 on show nights for pickups before the 7:30 curtain. Either a chicken caesar salad ($15) or a cheese and charcuterie platter ($20) come with toasted bagels and a drink. It’s a popular option. Charly told me that he’ll have orders for 30 to 50 on a good day.

The Levitt Pavilion doesn’t suggest any picnic providers on their website, but why would they in a food town like Westport? Everyone there has a few favorites for take-out that will more than fill the bill for a picnic. Like Shakespeare on the Sound, there is no reserved seating at their free concerts, so the early picnicker gets a good spot. There is an on-site concession selling beer and wine.

Our neighbor Gregg usually gets to the Levitt a few times over the summer. His favorite picnic is home cooked, but he has been known to stop at Los Poblanos on Westport Avenue on the way for some authentic Mexican food.

In addition to restaurant pickup, you can put together a sumptuous picnic by taking a quick cruise through either Whole Foods or Trader Joe’s.

Cava in New Canaan

We used to have an annual gathering of friends and a picnic dinner at the Summer Theater of New Canaan. Everyone brought something including that picnic staple, fried chicken. The company has moved to a new location close to town at 56 South Avenue. near the library for their season from July 5 to July 28.  Unfortunately, there’s no space for on-site eating, but they’re just a short stroll from some delicious dining around town. Seats in the tent are reserved, but in this case, the early bird gets the good parking spot.

Spiga pizza

We particularly like Spiga for their savory pizza and authentic Italian food. Cava is another good choice for its excellent selection of wines and a 10% discount for theater goers. Next door at Gates, there’s a special pre-theater dinner for $19.95.  You can see all the participating restaurants on the STONC website.

A performance under the stars with a picnic supper should be a part of every summer.  Just keep your fingers crossed on the weather.