Tompkins Square Park Greenmarket

East Village, Manhattan

Limited-time: Sundays year-round, plus Mondays June through November

View on map

The Monday farmers market spreads under the park's old elms, smaller and more neighborly than Union Square's sprawl. Early fall means heirloom tomatoes still warm from the sun, the first crisp apples, and bouquets of dahlias in colors that shouldn't exist in nature. Grab a coffee from the Crop to Cup stand and watch the regulars do their weekly rounds.

Insider tip. The Knoll Krest Farm stand has the best upstate apples—try the Macouns while they last.

Brooklyn Museum

Prospect Heights, Brooklyn

View on map

Cross into Brooklyn for the museum that always feels less crowded and more curious than its Manhattan counterparts. The Egyptian collection rivals the Met's, the contemporary galleries take risks, and the Beaux-Arts building itself is a stunner. September light pours through the glass pavilion, and the permanent collection rooms have that Monday-afternoon hush.

Insider tip. Don't skip the Visible Storage study center on the fifth floor—it's like the museum's fascinating attic.

Prospect Park

Prospect Heights, Brooklyn

View on map

Exit onto Eastern Parkway and walk into Olmsted and Vaux's masterpiece—the park they considered better than Central. September's golden hour starts early now, warming the Long Meadow and casting long shadows through the trees. Follow the path around the lake, where the willows trail in the water and the city feels very far away.

Insider tip. The Ravine on the park's east side is the city's last remaining forest—take the path down for a completely different atmosphere.

Al Di Là

Park Slope, Brooklyn

View on map

This Venetian trattoria has been an institution for over two decades, tucked on a quiet block where brownstone Brooklyn feels most itself. The handmade pasta is transcendent—tagliatelle with rabbit ragù, pappardelle with duck—and the seasonal antipasti change with what's good at the market. It's intimate, cash-only, and never feels rushed despite the no-reservations policy.

Insider tip. Arrive right at opening or be prepared to wait—put your name in and grab a drink at the bar at Benchmark across the street.

Harriet's Rooftop

Williamsburg, Brooklyn

View on map

Take the L train across to Williamsburg and ride the elevator to the top of the 1 Hotel for views that never get old—the entire glittering stretch of lower Manhattan reflected in the East River, the bridges strung with lights, Brooklyn spreading south. The cocktails are excellent, the crowd is grown-up without being stiff, and the breeze carries the first hint of real fall.

Insider tip. Request a seat at the northwest corner for the best unobstructed Manhattan view.