Outdoors in Central Park the Weekend of Sep 18–20, 2026

Stumblday's hand-checked ranking of the best outdoors in Central Park, Manhattan the weekend of Sep 18–20, 2026: 19 picks, refreshed weekly.

19 picks · checked Sep 7

#8Sat, Sep 19, 12:00 PM to Sat, Sep 19, 6:00 PM · Limited Run
That Guitar ManCentral Park: Hernshead, Manhattan
ManhattanLimited Run

That Guitar Man

David Ippolito has played free afternoons on the hill by Central Park's lake since 1992 — and this is his final season, so go.

#12
Osborn CupCentral Park: Bowling Green Lawn, Manhattan
Sun, Sep 20, 7:00 AM to Sun, Sep 20, 6:00 PM

Osborn Cup

White-clad bowlers contest the Osborn Cup on Central Park's manicured greens — a day of classic lawn bowling beside Sheep Meadow, free to watch.

ManhattanOne Weekend Only
#12Sun, Sep 20, 7:00 AM to Sun, Sep 20, 6:00 PM · One Weekend Only
Osborn CupCentral Park: Bowling Green Lawn, Manhattan
ManhattanOne Weekend Only

Osborn Cup

White-clad bowlers contest the Osborn Cup on Central Park's manicured greens — a day of classic lawn bowling beside Sheep Meadow, free to watch.

#15Sat, Sep 26, 9:00 AM to Sat, Sep 26, 7:00 PM · Limited Run
UnityMarketsNYCentral Park: 110th and Lenox, Manhattan
ManhattanLimited Run

UnityMarketsNY

An open-air market sets up at Central Park's 110th and Lenox corner — vendors, crafts and food at the Harlem gateway to the park.

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