Live music on Nantucket this week, August 17–23, 2026, venue by venue.
A platinum-selling rock band opens the week, a big band from another era lands midweek, and the free outdoor stage at Cisco runs every single day. Here's the full rundown.
The Muse — The Fray, Monday night
The headline show of the week: The Fray, with Colony House opening, on Monday, Aug 17. Doors at 7:00 PM, Colony House on at 8:00 PM, The Fray at 9:00 PM.
Friday, Aug 21 brings Michael Marcagi, the Midwestern singer-songwriter, to the same room.
Both at musenantucket.com.
Cisco Brewers — free live music every day
No cover, food trucks on site, outdoor stage:
Mon Aug 17 — Jacob & Jackson, 4–7pm
Tue Aug 18 — Bendigo Fletcher, 4–7pm
Wed Aug 19 — Bendigo Fletcher, 4–7pm
Thu Aug 20 — Jimmy Denny, 4–5pm
Fri Aug 21 — Doug & Co (12–3pm) and LowDown Brass Band (4:30–7pm)
Sat Aug 22 — Joshua Tree, 4–7pm
Sun Aug 23 — The Slips, 12–3pm
Friday is the one to plan around: LowDown Brass Band is a full horn section, and it goes on right as the afternoon crowd peaks. Full schedule at ciscobrewers.com.
The Chicken Box — late nights all week
Mon Aug 17 — Box Mondays, 10pm
Tue Aug 18 — Kashus Culpepper, 10pm, 21+
Wed Aug 19 — Kashus Culpepper, 9pm, 21+
Thu Aug 20 to Sat Aug 22 — Overserved Again, 10:30pm, a three-night run
Culpepper's two nights are the ones that will sell. Note the earlier 9pm start on Wednesday — it is not the same door time as Tuesday. Tickets and door details at thechickenbox.com.
Brotherhood of Thieves — Surf Bar sessions
Tue Aug 18 through Sun Aug 23 — Jacob & Jackson, a six-night run in the Surf Bar.
Monday is typically dark here, so Tuesday is the start. Sets usually run 8–10pm; confirm day-of at brotherhoodnantucket.com.
The Dreamland — the Glenn Miller Orchestra
Thursday, Aug 20 at 3:00 PM in the Main Theater: the Glenn Miller Orchestra, about an hour and twenty minutes of the big band era played straight.
It is the only afternoon show of the week that is not outdoors, and the only one where you sit down. Tickets at nantucketdreamland.org.
Something different: the Tuesday shanty cruise
Nantucket by Water runs its Sunset Cruise with the Shanty Singers on Tuesday nights through early September — a harbour cruise with live musicians leading sea shanties, which is a genuinely different night out from a bar stool. This week that is Tuesday, Aug 18. Book at nantucketbywater.com.
What's on tonight?
Mon 8/17 — The Fray with Colony House at The Muse (doors 7pm), Jacob & Jackson at Cisco (4–7pm), Box Mondays at the Chicken Box (10pm)
Tue 8/18 — Kashus Culpepper at the Chicken Box (10pm), Bendigo Fletcher at Cisco (4–7pm), Jacob & Jackson at Brotherhood, Shanty Singers cruise
Wed 8/19 — Kashus Culpepper at the Chicken Box (9pm), Bendigo Fletcher at Cisco (4–7pm), Jacob & Jackson at Brotherhood
Thu 8/20 — Glenn Miller Orchestra at the Dreamland (3pm), Jimmy Denny at Cisco (4–5pm), Overserved Again at the Chicken Box (10:30pm)
Fri 8/21 — Michael Marcagi at The Muse, Doug & Co and LowDown Brass Band at Cisco, Overserved Again at the Chicken Box
Sat 8/22 — Joshua Tree at Cisco (4–7pm), Overserved Again at the Chicken Box (10:30pm)
Sun 8/23 — The Slips at Cisco (12–3pm), Jacob & Jackson at Brotherhood
Before you head out
Two of this week's rooms are 21+ after 9pm, and the island runs out of parking long before the late shows start — bike, walk or take the shuttle if you can. Cisco and the Dreamland are the two genuinely all-ages options.
Stocking up first? Our shop is on Spearhead Drive, open until 7pm Sunday through Thursday and 8pm on Friday and Saturday, and orders placed online are ready for pickup in about ten minutes.
Times and line-ups come from each venue's own calendar and can change without notice — check the venue before you go.
Ready in ~10 minutes
Order online now — we'll text you when it's ready for pickup.