What's Up Cape's picks for Friday, September 18 through Sunday, September 20, 2026. The crowds thin out and the Cape gets good. Here's what year-rounders are actually doing this weekend. 19 picks made the cut this weekend.
Every listing below is hand-picked and vetted by our editors. Real locals. Real picks.
Friday, September 18
18
SEP
Osterville Historical Museum
Osterville Farmers Market
9:00 AM
18
SEP
The Pearl
The Rip it UPS!
3:00 PM · Free
18
SEP
O’Sheas Olde Inne
Joe MacDonald
5:30 PM · Free
18
SEP
Hog Island Beer Co.
The Boston Naturals
6:00 PM · Free
18
SEP
Neptune’s
Darling
6:30 PM
18
SEP
O’Sheas Olde Inne
Irish Whispa
8:30 PM · Free
Saturday, September 19
19
SEP
Orleans Farmers Market
9:00 AM
19
SEP
Ryder Street, Provincetown
Provincetown Farmers Market
9:00 AM
19
SEP
Harwich Community Center
Harwich Cranberry Arts & Music Festival
Sep 19 – Sep 20 · 11:00 AM
19
SEP
Cape Cod Fairgrounds
Cape Cod Brew Fest
2:00 PM
19
SEP
The Pearl
Johnny and the Value Leaders
3:00 PM · Free
19
SEP
O’Sheas Olde Inne
The Wildlife Band
5:30 PM · Free
19
SEP
Hog Island Beer Co.
Power Load
6:00 PM · Free
19
SEP
Wellfleet Preservation Hall
Isabelle O’Connell
7:00 PM · Tickets
19
SEP
O’Sheas Olde Inne
Billy & Bill
8:30 PM · Free
Sunday, September 20
19
SEP
Harwich Community Center
Harwich Cranberry Arts & Music Festival
Sep 19 – Sep 20 · 11:00 AM
20
SEP
The Pearl
Rob Glassman Band
3:00 PM · Free
20
SEP
O’Sheas Olde Inne
Sean Murphy’s Traditional Irish Music Session
4:30 PM · Free
20
SEP
Mattakeese Wharf
Jamie Wyeth
6:00 PM
20
SEP
O’Sheas Olde Inne
Fred Clayton’s Sunday Blues Jam
8:00 PM · Free