As the weather cools off, outdoor gatherings become more enjoyable—the sun isn't as strong, the insects aren't as pesky, and there's a beautiful crispness in the air. I like to switch things up, bringing the indoor out and enjoying laid-back gatherings on the rooftop. While I love picnics, they are usually far from home and involve lots of packing, lugging around supplies, getting the right food and drink, and then keeping it fresh. And I always seem to forget something! The rooftop offers a unique and convenient alternative with all the charm and fun of a traditional picnic.
In the autumn, the sun is shining and the weather is cooler, so my favorite time of day would be lunch or brunch; however, if you have power and lighting up there, you can bring this right into evening.
There's no need to be formal with invites unless you are hosting for a specific event like a shower or a birthday. Sending a quick Paperless Post invite or texting groups of friends is usually my go-to for this type of casual entertaining. To determine how many guests you can fit, start by ensuring your rooftop is safe and level, then work backwards from there. I divide any event space into two sections—half for standing and half for sitting, so there's room to roam around as well as sit.
Rooftop dining is an easy option for entertaining—picnic-style food can be prepped ahead of time. If it's a potluck, I take my guests into consideration. If the friends and family I'm inviting love to cook, I will ask them to cook and share. (Tip: Suggest a specific course to guests so you have a balanced meal and not too much overlap.) Otherwise, I just ask everyone to bring a bottle of wine.
I always make sure that the food is easy to transport, in true picnic style, and that items can be made and packaged in advance to take the stress off the prep and put the focus on creating a beautiful setting. The food should be served family-style so it's easy to grab and eat for this picnic event, and I create smaller portions so guests can try a little of everything. Seasonal ingredients, like apples, squashes, and greens, are the starting point for my menu.
I like to start with a grazing platter. Not only do they double as decoration, but they're also an easy way to create a table of vibrant fall colors, textures, and flavors that appeal to the eyes and the taste buds. That's why I love making grazing platters. A selection of meats, fresh fruits, dehydrated vegetables, and cheeses are always crowd-pleasers and the perfect way to start the meal.
Fall officially kicks off soup season, so I like to serve warming bowls of Smoky Sweet-Potato Soup or another vegetarian option. I heat it on the stovetop, then pour it into an enamel teapot or thermos—that keeps it warm and makes it easy to transport and serve. I put pumpkin seeds on the grazing platter for a garnish for soup and to add some crunch. And what pairs better with a soup that a bright, green salad? In the fall, I often opt for a combination of leafy greens with seasonal fruits and vegetables. I like serving the salad in metal bowls—refrigerate the bowls first, and they keep your salad cool longer.
Quiche is another easy option for a picnic. Fold your favorite fall ingredients into a quiche, an easy, high-protein crowd-pleasing option. Whatever you do, make it ahead of time—it actually tastes better the next day. Plus, it travels well and can be served warm or cold.
If I want to serve sandwiches, classic baguettes are my go-to as they don't get soggy, take minutes to make, and are travel-ready. I wrap them with kraft paper (or cutting a paper bag) and tie them with classic twine or thin rope. It makes them easy to transport, pick up, and eat.
To round out the meal, a simple, moist carrot cake with cream cheese frosting is the dessert I like best. This tried-and-true confection is endlessly cravable and can be made in a loaf or a tiered naked cake for a special occasion. Hankering for a classic outdoor dessert like s'mores? This portable favorite is a fun twist: Use a classic hot chocolate base and load it up with marshmallows and a vanilla simple syrup, topped with crumbled graham crumbs.
Setting up a drink station takes the stress out of bartending. I create a designated section for drinks (as I did here, using stacked vintage crates) and stock it with essentials so everyone can help themselves. I make sure I have a variety of alcohol, nonalcoholic, hot, and cold to keep everybody happy. Fall-infused cocktails like bourbon-cider are my go-to. Fill vintage milk jugs with water and juices, and use large enamel bowls as ice buckets for chilling wine and beer.
The Setting and Seating
For a quick DIY table, I use wood crates and pallets as eating surfaces (test for splinters first!). Old doors or sheets of plywood also work. And forget chairs, there's something much more intimate and cozy about sitting on the floor, so I bring various textiles and seating options outside. Once the roof surface is clean, I put down old towels and sheets, then I arrange throws, rugs, and bed and couch cushions of various sizes. As this picnic is on a hard, concrete surface, the bigger and thicker the better—layer them together for extra comfort. Ottomans, beanbag chairs, or other low seats add a rich textural element, and comfortable cushions encourage guests to linger at the table. I also fill a basket with extra throws and blankets, as fall afternoons can turn a little chilly.
Rooftop entertaining has the ease of a picnic with the flair of outdoor dining. You also have a blank canvas, so you can get very creative. Market baskets are useful to schlepp items from the kitchen to the rooftop and can double as decor. (I love baskets from Vivi Et Margot as they also have over-the-shoulder handles.) For the tabletop, don't use your best glasses and fragile plates—opt for things that are durable. Vintage enamelware, metal bowls, and wood items are a must. A few large trays for carrying food and beverages are helpful, and I use enamel or insulated pitchers for hot drinks and soups. Small baskets can double as serving bowls, and classic paper bags can quickly be rolled down and turned into great disposable bread baskets.
To minimize cleanup, opt for cool disposables and wood cutlery (it can be easily customized for place cards as well, with some snazzy Sharpie calligraphy). I love Bambu's beautiful disposables—they look just like wood and give a seasonal rustic touch to the table. I like mixing and matching glassware for a more casual vibe. Mason jars and old milk bottles are durable, cost-effective glassware for the outdoors and perfect for drinks both hot and cold. Whatever you do, don't skip the flowers just because you're picnicking! A centerpiece made with dried grasses, florals, and greens adds a rustic feel and natural beauty to your tablescape—and will last all season.
Music matters here, too. Being on a rooftop gives you a tranquil view of the city. I keep my playlist and vibe relaxing as a contrast to what's going on below. The Coffee House or Acoustic Covers are perfect for a chilled-out afternoon. Bring a portable speaker up to the roof to make your job even easier. Sonos makes a great one you can connect easily to your phone and bring with you anywhere.
Photos: Arianna Tettamanzi
Florals: East Olivia
Linens, Boards & Baskets: Vivi et Margot
Calligraphy: Eterate Calligraphy
Dress: Love Shack Fancy