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UrbanSitter Chicago Events
Drop-off Thursdays at Purple Monkey Playroom
Every Thursday | 10:00 AM – 12:30 PM
Purple Monkey Playroom | 2040 N. Western Ave.
Need a break? Register to drop off your children ages 6 months+ for care at the Purple Monkey Playroom. UrbanSitters will be there to welcome and play with your children! You can even prepay for snacks for your little one to munch on during the visit!
Registration: Visit the registration page to sign up or call Purple Monkey at 773-772-8411 for
NPN’s Annual Roscoe Village Halloween Party
Thursday, October 23 | 4:00 – 6:00 pm
Little Threads | 2033 W. Roscoe
Parents and kids are invited to meet, mingle, eat some goodies, show off their costumes, have their face painted by UrbanSitters and hear the wonderfully entertaining Storybook Mom, Nili! Little Threads is also offering 20% off purchases which is amazing because they have the most adorable things – great time to stock up on holiday outfits and gifts!
BCBoo Little Monster Mash Halloween Bash
Sunday, October 26 | 10:30 am – 1:00 pm
Lincoln Hall | 2424 N. Lincoln Ave.
Enjoy live performances by Ben Tatar & the Tatar Tots, trick or treating, gift bags, cupcake decorating, costume contests and face painting by UrbanSitters!
UrbanSitter Los Angeles Events
UrbanSitter New York Events
West Side Y’s Fit for All 5K & Boo Fest
Saturday, October 25 | Race starts at 8:00 am
Riverside Park | 108th Street Terrace
Get your running shoes on and help fight childhood obesity! 100% of the proceeds support childhood obesity and youth diabetes prevention program. Stop by the UrbanSitter table for some awesome face painting by UrbanSitters!
Harlem 4 Kids Halloween Family Disco & Fundraiser
Saturday, October 25 | 11:00 am – 1:00 pm, Parade starts at 1:00 pm
Harlem Center PAL Building | 441 Manhattan Ave.
Arrive in costume and enjoy activities for children of all ages, as well as face painting, crafts with UrbanSitters, a DJ spinning the hits, and more!
PS 87 Harvest Fest
Saturday, October 25 | 2:00 – 6:00 pm
PS 87 | 160 West 78th Street
Don’t miss this fun fall festival featuring yummy treats and a spooky craft at the UrbanSitter table!
The PS 39 Halloween Spooktacular
Saturday, October 25 | 5:00 – 8:00 pm
John Jay Cafeteria | 237 7th Ave.
Join us for a scary good time at PS 39’s Halloween Spooktacular! Be sure to stop by the UrbanSitter table for a spooky craft and to meet local babysitters!
Friends of Bleecker Playground Halloween Festival
Sunday, October 26 | 10:00 am – 2:00 pm
Abingdon Square Park
The toddler parade starts at 10am then enjoy the free festival featuring hay rides, face painting by UrbanSitters, cupcake decorating and much more!
Hip Tot’s Halloween Hullabaloo
Sunday, October 26 | 12:00 – 3:00 pm
Greenwood Park | 555 Seventh Avenue, Park Slope
Enjoy a free day of fun featuring crafts, a costume parade, games and face painting with UrbanSitters!
UrbanSitter San Francisco Bay Area Events
Marin: Mill Valley Trunk or Treat
Wednesday, October 22 | 5:00 – 6:45 pm
Mill Valley Community Center | 180 Camino Alto, Mill Valley
Come visit UrbanSitter’s trunk for arts & crafts and treats in the 1st annual Trunk or Treat event at the Mill Valley Community Center. This will be held in between the Annual Music & Magic Show times at 4pm & 6:30pm.
San Francisco: Preschool Preview Night
Wednesday, October 22 | 5:30 – 7:30 pm
San Francisco County Fair Building (Hall of Flowers) in Golden Gate Park
Preschool Preview Night showcases over 100 preschools, childcare centers, resource agencies, and child-related service providers. Talk one-on-one with representatives from schools, and find the best preschool match for your child. Be sure to stop by the UrbanSitter table!
San Francisco: DayOne Baby In-Store Meet & Greet
Friday, October 24 | 3:30 – 5:00 pm
DayOne Baby | 3548 Sacramento Street
Stop by the DayOne Baby store to talk with UrbanSitter parent reps and meet local sitters! Then join DayOne’s FREE story time at 3:00 pm for ages 1 month to 2 years.
Peninsula: California Ave. Trick or Treat & Blossom Halloween Carnival
Sunday, October 26 | 10:00 am – 2:00 pm
S. California Avenue, Palo Alto
Come start off your Halloween celebrations on California Ave: Palo Alto’s most popular event for the whole family! Halloween-themed crafts by UrbanSitter! Trick or Treating at businesses on California Ave (between El Camino Real and Park Blvd), musical performances, costume parade & contest, and carnival games!
San Francisco: Birth and Baby Fair
Sunday, November 2 | 10:00 am – 4:00 pm
Herbst Pavilion at Fort Mason
Don’t miss the PREMIER event for new and expecting parents! The Birth and Baby Fair showcases local businesses and resources as well as independent designers with the aim to educate and expose new & expecting parents and young families to unique & beneficial products & services. Stop by the Tot Spot play area sponsored by UrbanSitter!
Marin: power Play Meet & Greet
Wednesday, November 5 | 9:30 – 11:30 am
CalStar Gymnastics | 70 Digital Drive, Novato
UrbanSitter will be at Power Play to introduce you to some new sitters! We’ll have some arts & crafts for when your kids need a break from the gym.
San Francisco: UrbanSitter Babysitter Meet & Greet at Aldea Baby
Saturday, November 8 | 9:00 – 11:30 am
Aldea Baby | 1017 Valencia Street
UrbanSitter and Aldea Baby are teaming up for a Babysitter Meet & Greet where you can meet great local SF babysitters. Come by for some discount to Aldea Baby and get to know a few sitters who are looking for babysitting jobs this fall.
San Francisco: Speed Sitting with UrbanSitter & Peekadoodle
Saturday, November 15 | 10:30 am – 12:00 pm
Peekadoodle Kidsclub | 900 North Point Street f100
UrbanSitter and Peekadoodle are teaming up to hold a special event to help you find a fabulous new babysitter! You can quickly meet and interview a host of local sitters and find the perfect fit for your family. Meet them in person, then book them online anytime!
UrbanSitter Washington D.C. Area Events
Baby Loves Disco
Friday, October 24 | 11:00 am – 1:30 pm
Rock N Roll Hotel | 1353 H St. NE
Head on over to the Rock n Roll Hotel for a family friendly Halloween-themed disco party! Show off your dance moves and have the chance to meet some local sitters at the UrbanSitter table!
Turtle Park Halloween Parade
Friday, October 24 | 5:00 – 8:00 pm
Turtle Park | 45th Street NW & Van Ness NW
Strut your stuff at the Halloween Parade in Turtle Park! This local favorite features games, pizza, a free movie and crafts!
4th Annual Little Goblins Parade
Saturday, October 25 | 12:30 – 4:00 pm
Assemble at Stead Park
Wear your best costumes to march in the parade from Stead Park to Logan Circle and trick or treat at local businesses along the way. The party continues in Logan Circle with live music, entertainers and halloween themed activities! Come by the UrbanSitter table to make some spooky Halloween crafts!
Babysitter Meet & Greet at Menchie’s
Wednesday, October 29 | 7:00 – 8:30 pm
Menchie’s Frozen Yogurt | 1939 12th Street NW
UrbanSitter and Menchie’s are teaming up for a Babysitter Meet & Greet where you can meet great local DC babysitters. Come by for some delicious frozen yogurt and get to know a few sitters who are looking for babysitting jobs this fall.