Cheer Her On Weekend is an opportunity to grab a gal pal and explore the beauty of New England.


With guided walks through historic farmland, scenic coastlines and exploring the quaint small towns of Boston’s North Shore, you’ll have a chance to reconnect with that friend you’ve been looking to adventure with (or come solo to meet new friends!) and rediscover that joy is still part of your story—even in the winter! Join us for two packed days that include: good meals, breathtaking scenery, creative activities, cozy spaces, hearing from our special guest Sara Groves.

Who: Women 16 and up who want to grab a friend and have a good time!
What: A chance to reconnect with others and meet some new friends, too!
When: February 8-9, 2025
Why: Why not?
Where: North Shore of Boston, MA

Here’s how it works: You’ve always wanted to go to New England and now you get a guided opportunity. And the best part? You can grab a friend to join you and make it a girl’s weekend! We’re keeping it inexpensive so that you can get the most bang for your buck. You cover travel and lodging (and trust us, there are some FUN places to stay in all kinds of price ranges) and we’ll organize a weekend you’ll never forget.

What You Pay: 450.00

What You Get: Two days of curated experiences, historic tours, guided coastal excursions, some good meals, after-hours antiquing, and a Sara Groves concert in a venue you will LOVE.
You just show up and we’ll do the rest!

Meet Our Guest: Sara Groves

Sara Groves is a 25+ year veteran singer/songwriter and recording artist. Sara’s last full release, What Makes It Through, is loosely based on the writings of Kazuo Ishiguro, and is a reflection on the stories we tell ourselves, and the role these stories play in reconciliation. In the fall of 2024, Sara remastered Add To The Beauty for vinyl and CD that featured three new songs (not available on streaming until 2025). In 2011, Sara and her husband Troy opened a unique community art center, Art House North, in a 100+ year old church. Troy and Sara live in St Paul with their grown and growing children, Kirby, Toby and Ruby.

FAQ’s

  1. Who is this for?

    • This is for the woman who wants to be refreshed, inspired, and meet new friends. Whether you come with a pal or by yourself, you’ll have new buddies by the end of this. It’s designed to be fun or everyone. Also, we will be doing a few creative exercises so this is a perfect trip for someone wanting to connect to the beauty of creative work in the middle of winter.

  2. Can I bring my family or kids?

    • We love families and kids, but we have limited space so we ask that only nursing babes or children under a year join you. Our age minimum for the trip otherwise is 16 years-old, so you can bring a gal who is older than that!

  3. How do transportation and housing work?

    • The closest airport is Boston Logan International Airport in Boston, Massachusetts. We will travel around the north shore and Essex County during the weekend. While attendees are able to book anywhere they’d like for overnight accommodations, we will provide a list of recommended places as well as connect participants in a Facebook group so they can potentially carpool or share a place to stay! You’ll want a car, whether sharing with friends or other attendees. Uber is not recommended. We suggest you book SOON because accommodations in Massachusetts fill up fast. Reach out to us at cheerheron@gmail.com if you have any questions!

  4. What should I wear?

    • Winter in New England is about layers. Things will be pretty casual so no need for formalwear. Will it be crisp? That’s likely. Will it be beautiful out? You bet. Is anything possible? Entirely. Hats, gloves, good boots and warm socks are a win. Also, we’ll give you a full packing list well before you arrive!

  5. Is the event virtual?

    • Sadly, (and happily!) no, it is not. This is for gathering and being together in person.

  6. Can I get a refund?

    1. We do provide a full refund (minus processing fees from Eventbrite) up until 30 days before the event. (January 8 at 12pm ET)

Still got questions? Fill out the form below and we’ll get ‘em answered!