Tommy Wotruba
7pm Sat. Oct. 3
Harbor Rail Pub, Two Harbors
Saturday, Oct. 3rd, 2026
Brothers Burn Mountain
8pm Sat. Oct. 3
Gunflint Tavern, Grand Marais
Saltydog
8pm Sat. Oct. 3
Up Yonder on 61, Grand Marais
Sunday, Oct. 4th, 2026
Art Along the Lake
10am-5pm Sun. Oct. 4
Multiple locations, Grand Marais
KTWH Music Series: Shane Nelson, Laamar
3-5:30pm Sun. Oct. 4
Castle Danger Brewery, Two Harbors
Bump Blomberg
3-6pm Sun. Oct. 4
Gunflint Tavern, Grand Marais
Sing & Bring: Big Stage Karaoke & Community Potluck
3-7pm Sun. Oct. 4
Harbor Theater, Two Harbors
Spruce Roots
3:30-5:30pm Sun. Oct. 4
North Shore Winery, Lutsen
Sunday Guitar Pull
7:30-9:30pm Sun. Oct. 4
Caribou Highlands, Lutsen
Tuesday, Oct. 6th, 2026
Eric Frost
4:30-6:30pm Tue. Oct. 6
North Shore Winery, Lutsen
Yuya Mix
5:30pm Tue. Oct. 6
Two Harbors Public Library, Two Harbors
Open stage
6-9pm Tue. Oct. 6
Up Yonder on 61, Grand Marais
Wednesday, Oct. 7th, 2026
Joe Paulik
6-9pm Wed. Oct. 7
Gunflint Tavern, Grand Marais
Royal Temper Tantrums that have Changed History
6:15-8pm Wed. Oct. 7
Johnson Heritage Post Art Gallery, Grand Marais
Thursday, Oct. 8th, 2026
'Superior: A 50-Year Photographic Journey' with Craig…
5:30-6:30pm Thu. Oct. 8
Two Harbors Public Library, Two Harbors
Gordon Thorne
6-8pm Thu. Oct. 8
North Shore Winery, Lutsen
Open mic
6-8pm Thu. Oct. 8
Larsmont Trading Post, Two Harbors
Charlie Roth
6-8pm Thu. Oct. 8
Cascade Lodge, Lutsen
Briand Morrison
6pm Thu. Oct. 8
Gunflint Tavern, Grand Marais
Friday, Oct. 9th, 2026
Grand Marais Apple Festival
6-7:30pm Fri. Oct. 9
The Hub, Grand Marais
John Cron
6-9pm Fri. Oct. 9
Ledge Rock Grille, Two Harbors
Bruce Bednarchuk
6pm Fri. Oct. 9
Larsmont Trading Post, Two Harbors
Bump Blomberg & Gordon Thorne
7pm Fri. Oct. 9
Silver Bay Lounge, Silver Bay
Squid City Slingers
8pm Fri. Oct. 9
Gunflint Tavern, Grand Marais
Jojo Green
8:30pm Fri. Oct. 9
Up Yonder on 61, Grand Marais
Saturday, Oct. 10th, 2026
Grand Marais Apple Festival
10am-7pm Sat. Oct. 10
The Hub, Grand Marais
North Shore Oktoberfest
noon-6pm Sat. Oct. 10
Bluefin Bay, Tofte
'Superior: A 50-Year Photographic Journey' with Craig…
2-3pm Sat. Oct. 10
Johnson Heritage Post Art Gallery, Grand Marais
Birch Bark Canoe: History, Construction & Use
2-3pm Sat. Oct. 10
Chik-Wauk Nature Center, Grand Marais
Hannah Rey
6-9pm Sat. Oct. 10
Ledge Rock Grille, Two Harbors
Author Talk with Emily Stone
6pm Sat. Oct. 10
Drury Lane Books, Grand Marais
Bizhiki
7pm Sat. Oct. 10
Arrowhead Center for the Arts, Grand Marais
Squid City Slingers
8pm Sat. Oct. 10
Gunflint Tavern, Grand Marais
Jojo Green
8:30pm Sat. Oct. 10
Up Yonder on 61, Grand Marais
Sunday, Oct. 11th, 2026
Fall Fun Run
noon Sun. Oct. 11
Cutface Creek Wayside Rest, Grand Marais
Bump Blomberg
3-6pm Sun. Oct. 11
Gunflint Tavern, Grand Marais
Sunday Guitar Pull
7:30-9:30pm Sun. Oct. 11
Caribou Highlands, Lutsen
Tuesday, Oct. 13th, 2026
Eric Frost
4:30-6:30pm Tue. Oct. 13
North Shore Winery, Lutsen
Open stage
6-9pm Tue. Oct. 13
Up Yonder on 61, Grand Marais
Wednesday, Oct. 14th, 2026
Joe Paulik
6-9pm Wed. Oct. 14
Gunflint Tavern, Grand Marais
Thursday, Oct. 15th, 2026
Gordon Thorne
6-8pm Thu. Oct. 15
North Shore Winery, Lutsen
SonofMel
6-8pm Thu. Oct. 15
Cascade Lodge, Lutsen
Open mic
6-8pm Thu. Oct. 15
Larsmont Trading Post, Two Harbors
North Shore Community Swing Band
6:30-8:30pm Thu. Oct. 15
Up Yonder on 61, Grand Marais
Friday, Oct. 16th, 2026
Artist talk: John Hitchcock
4:30-5:30pm Fri. Oct. 16
Grand Marais Art Colony, Grand Marais
Family Fun Night & Lantern Walk
5-8pm Fri. Oct. 16
North House Folk School, Grand Marais
Saturday, Oct. 17th, 2026
Artist Molly Siebenaler
10am-6pm Sat. Oct. 17
Split Rock Lighthouse, Two Harbors
Sunday, Oct. 18th, 2026
Sunday Guitar Pull
7:30-9:30pm Sun. Oct. 18
Caribou Highlands, Lutsen
Tuesday, Oct. 20th, 2026
Eric Frost
4:30-6:30pm Tue. Oct. 20
North Shore Winery, Lutsen
Open stage
6-9pm Tue. Oct. 20
Up Yonder on 61, Grand Marais
