Retreats

by Go with Jenny O

A new way to Go

These aren't your typical wellness retreats with packed schedules or specific goals. Instead, think cozy weekends where you can finally finish that book, try your hand at a new craft, play a board game, and start a meaningful conversation with a friend that seems impossible to find time for in your daily life.

The purpose of these retreats is to allow you space, even just for a weekend, to trade screen time for quality time and rediscover the joy of offline connection.

I'm launching with two retreat weekends, each specially designed to bring together women of similar life stages. While there are suggested age ranges, you can choose the weekend that most resonates with you personally.

Two Retreats. Two Opportunities to Relax.

  • 20s & 30s Retreat: Nov 14-16, 2025

    - A community-focused getaway for young adults craving real connection

    - Meet like-minded peers who value friendship and personal downtime

    - Perfect for those wanting to expand their social circle beyond work and dating apps

    Tell Me More

  • 35+ Retreat: Jan 30 - Feb 1, 2026

    - A rejuvenating escape designed for women seeking deeper connection

    - Guilt-free time to prioritize yourself and new relationships

    - Build lasting friendships with women who understand your season of life

    Let's see the details

We all know that making friends as an adult is hard. These retreats are for building community as much as they are for you to take a break.

Registration

Registration opens on Friday, August 15!

Registration for Retreats by Go with Jenny O will function on a wait list system.

This is so we can make sure the rooms are filled accurately and efficiently, with an eye for safety! 

To register, you will complete an application form which will automatically put you on a wait list. This form will be sent out to my email list on Friday, August 15th at 10 AM ET. When you are moved off the wait list, you will receive an email from jenny@gowithjennyo.com inviting you to confirm your spot by paying your registration fee. Once you receive your invitation to confirm your spot, you will have 48 hours to make your payment, otherwise your spot will pass to the next person on the list.

Members of my email list will receive first access to the registration form! To sign up for my email list, click here. To make sure that none of the emails go to spam, add jenny@gowithjennyo.com to your contacts!

 FAQs

  • Check in begins at 2 PM on Friday. Our first activity together will be welcome drinks and icebreakers at 6:30 PM. Our first shared meal will be dinner on Friday, so we recommend stopping for lunch on your way.

    Friday afternoon is yours for relaxation and getting settled if you so choose. If you are going to be arriving later than 6 PM, please let us know in advance.

    Departure is at 10 AM on Sunday following breakfast. If you want to extend your mountain weekend, we will provide recommendations for nearby activities and brunch/lunch spots.

  • Both retreats are in the Pocono Mountains in PA! For specifics on each retreat’s location, please visit the specific pages about each weekend. 20s & 30s weekend can be found here, while 35+ weekend can be found here.

  • Transportation is not included in the cost of the retreat. However, we will provide opportunities for the group to connect in advance and arrange carpools if you so choose.

  • Pricing includes accommodation for Friday and Saturday night, as well as food and drinks, activities, and more! Transportation is not included. See the individual retreat pages for more information! Click here for the 20s & 30s retreat. And click here for the 35+ retreat.

  • Nope! Our beautiful airbnb accommodations have got you covered!

  • A packing list will be provided at least 4 weeks prior to the retreat.

  • Absolutely! There are opportunities for private rooms, as well as shared spaces where we will pair you with roommates. This is an opportunity to build a community and make new friends, so whether you come solo or with friends, you will be welcomed.

  • Each person will need to complete the registration form individually! There will be a spot on the form for you to indicate who you are signing up with. As long as you write that you are attending together, we will know you intend to room together. Groups of friends that are requesting to share a room will be moved off of the wait list together! If you are signing up for separate rooms, we cannot guarantee you will all be moved off of the wait list at the same time.

  • You must be at least 21 to attend. While there are age ranges for each retreat weekend, there is no age limit for attending (just as there is no age limit on girlhood!). Contact us if you'd like to discuss further.

  • Yes! There will be a Zoom get to know you event. If the group desires, we can also arrange an in person opportunity to gather and begin building community in advance of the retreat. These are fully optional experiences!

  • While phones are allowed, we will invite you to "disconnect to connect" by giving your phone a nap for as long as you're comfortable. In this way, we can disconnect from the "doom scroll" and connect with each other and ourselves!

  • Comfort food is the name of the game here. We're having a slumber party after all! While we'll treat ourselves with one private chef dinner, we'll also have a pizza party (because, balance). We will work to accommodate dietary restrictions as best we can, but if you have concerns about this, please reach out!

  • Alcohol (wine and seltzer) will be provided in limited quantities and is included in your cost, but please be aware that this is not the focus of this retreat. Please do not BYOB any additional alcohol.

  • This policy extends to ALL reasons for cancellation without exception. If you are concerned about the financial risk, we recommend you purchase cancellation/trip insurance. Some recommended travel insurance carriers are Arch RoamRight and Allianz. You can also check various rates on travelinsurance.com.

    For cancellations made at least 30 days prior to the event, you will receive a full refund.

    For cancellations made between 14-29 days prior to the event, you will receive a 50% refund.

    Cancellations made less than 14 days prior to the event are non-refundable.

    Registrations may be transferred* to another person at no charge. Transfers are not complete until new registrant completes full registration and any outstanding payment has been made (if applicable).

    If you do not attend, arrive late to or leave early from the retreat, no refund or credit will be issued.

    No exceptions to these conditions apply.

  • Travel insurance is always a great choice, for any type of trip.

    Unforseen and unfortunate circumstances (death in the family, illness, etc.) can happen to anyone. Travel insurance can help offset this risk.

    We also recommend that you thoroughly read our terms & conditions prior to checkout. You must agree to these terms during the registration process. The refund/cancellation policy will be enforced for all reasons for cancellation without exception.

    Some recommended travel insurance carriers are Arch RoamRight and Allianz. You can also check various rates on travelinsurance.com.

  • Yes! The hope is that there will be many more to come. You can also contact Go with Jenny O if you are interested in planning a retreat for your specific group (i.e. book club, bachelorette party, moms group).

  • We are happy to help! Please send us an email at jenny@gowithjennyo.com.