Milwaukee Weekend Guide: Sept. 22-24 | Milwaukee Magazine

14 Things to Do in Milwaukee This Weekend: Sept. 22-24

Check out Harbor Fest, an apple market, a fair of four-legged friends and more.

1. Nathaniel Rateliff & The Night Sweats

FRIDAY AT 6:30 P.M. | BMO PAVILION 

Soulful folk singer Nathaniel Rateliff and his R&B band take to the BMO Pavilion this Friday night. Rateliff is known for his true-to-life lyrics and vintage rock sound, with hits such as “S.O.B.,” “You Worry Me,” and “A Little Honey.”

2. Jay Pharoah at Milwaukee Improv

ALL WEEKEND AT VARIOUS TIMES | MILWAUKEE IMPROV 

Known for his spot-on impressions and being a cast member on Saturday Night Live, Jay Pharoah brings his impressive range of comedy experience to MKE. The Virginia-born comedian covers pop culture, politics and more in his stand-up routines. 

3. William Kent Krueger

FRIDAY AT 7 P.M. | SHARON LYNNE WILSON CENTER FOR THE ARTS

Mystery author William Kent Krueger comes to Brookfield to discuss his latest book, The River We Remember. Admission to the event includes a copy of the riveting novel about a small Minnesota town in the ’50s upturned when a wealthy landowner is found dead in the river.


Tell us who you’d pick to be a Betty this year!

 

4. GIL Jazz Combo

FRIDAY AT 8 P.M. | BAR CENTRO 

A combo of celebrated, well-known local musicians performs in the cozy atmosphere of this Riverwest bar for a night of jazz. Keep an eye (and ear) out for founder Joel Lehman’s flumpet – an instrument that’s a blend of trumpet, cornet and flugelhorn.

5. Apple Harvest Festival

SATURDAY AT 9 A.M. | RETZER NATURE CENTER 

Take a tour of this Waukesha festival’s Apple Market, which offers over 30 varieties of the namesake fruit as well as cider from Brightonwoods Orchard and Patterson Orchards. It’ll also include a beer garden, live music, planetarium shows, arts and crafts and a scarecrow-themed scavenger hunt to stir one’s autumn spirit.

6. Fromm Petfest

SATURDAY AT 10 A.M. | HENRY MAIER FESTIVAL PARK 

Grab your leashes – this annual celebration gives pet owners a chance to connect with one another and treat the dogs and cats they love. The free event will have agility courses, a pet-themed marketplace, shows, family activities and many furry friends to meet.

Two very good boys, or girls, survey the festival grounds; Photo courtesy of Fromm Petfest

7. Rugby World Cup Watch Party

SATURDAY AND SUNDAY AT 10:45 A.M. | COUNTY CLARE INN & PUB 

It’s game on as County Clare Inn & Pub hosts Rugby World Cup watch parties for England v. Chile, South Africa v. Ireland and Scotland v. Tonga. The Irish bar boasts menu items such as Reuben rolls, corned beef sandwiches and more to dine on while cheering for your favorite team.

8. Waukesha Oktoberfest

SATURDAY AT 12 P.M. | FRAME PARK 

The seventh annual Waukesha Oktoberfest offers German fun in the city’s beautiful Frame Park. Food, beer, cornhole contests, glass stein blowing and maasskrugstemmen – or stein holding – can be found at this family fall festival.

9. Barbie Beach Party

SATURDAY AT 2 P.M. | NOMAD WORLD PUB 

Still have Barbie fever? At Nomad World Pub’s Barbie Beach Party, guests are encouraged to come dressed as Barbie or Ken and enjoy dunk tanks, beach balls, kiddie pools, prizes and a “beachside” barbecue.

10. Doors Open 2023

SATURDAY AND SUNDAY AT VARIOUS TIMES | VARIOUS LOCATIONS THROUGHOUT MILWAUKEE 

Organized by Historic Milwaukee, Doors Open is an annual chance to explore historic Milwaukee buildings, many of which are normally closed to the public. The event features over 130 locations in which to explore and is an exciting chance for any curious mind to experience a new neighborhood and a dose of Milwaukee history.

11. Bean Plant Block Party at Anodyne Coffee

SUNDAY AT 1 P.M. | ANODYNE COFFEE, WALKER’S POINT

For the second year, skate ramps and obstacles for bikes and boards will be staged outside Anodyne Coffee for all riders to show off their skills. The event comes complete with food trucks, beer, live music and, of course, coffee.

12. Harbor Fest

SUNDAY AT 11 A.M. | HARBOR VIEW PLAZA

The Harbor District’s festival celebrates Milwaukee’s maritime history and vibrant lakefront. Watch a parade of artistic floats on the Milwaukee River and the release of a lake sturgeon into the water. There’ll also be food, boat tours, chalk art, a rock wall, a bounce house, face painting, dancers and more.

The UW Milwaukee School of Freshwater Sciences in the Harbor District; Photo courtesy of Visit Milwaukee

13. Beethoven 5 at the Milwaukee Symphony Orchestra

ALL WEEKEND AT VARIOUS TIMES | BRADLEY SYMPHONY CENTER 

The orchestra opens the new season with Beethoven’s famous Fifth Symphony and a mix of classic and contemporary works. Bass-baritone and Milwaukee Symphony Orchestra’s new artistic partner Dashon Burton will sing selected songs from Schubert and a song cycle of poems set to strings by Jamaican composer Eleanor Alberga.

14. Dad’s Season Tickets

THURSDAY THROUGH SUNDAY AT VARIOUS TIMES | SUNSET PLAYHOUSE 

Sunset Playhouse presents the musical comedy Dad’s Season Tickets, which tells a story about three daughters who scheme to inherit valuable Packers season tickets. It’s the last weekend to see this show geared toward football fans, musical enthusiasts and anyone who understands putting family first.


Want more great Milwaukee events? Check out our calendar