About us
Hello! Jackie here. 🌿
My goal and hope for this group is to bring the LGBTQIA+ community together — along with folx who value inclusion — to enjoy the beautiful outdoors here in Western Connecticut while building genuine, fun connections. This is intended to be a safe, welcoming space where folx from all walks of life, shapes and sizes, fitness levels, and identities can come together to explore the amazing trails right in our own backyards.
The pace of our hikes will always be set by the slowest hiker (and that may very well be me!). The spirit of this group is supportive, encouraging, and judgment-free. Whether you’re looking to get back into movement, build confidence, or simply enjoy nature with good company, you are welcome here.
A little about me: I moved to Connecticut after living in the Boston area for over 30 years, landing in Litchfield in October 2020. While I’ve explored some of this trail-filled region, I know I’m far more motivated — and consistent — when I’m doing it with others. Creating and leading this group is a commitment to myself and to community. Our hikes typically range from 3–4 hours, starting out easy and gradually moving into more moderate terrain over time.
If you’re an advanced or very fast hiker, this may not be the right fit — but if you enjoy moving at a steady, inclusive pace and value connection as much as the destination, we’d love to have you.
✨ What’s new for 2026:
This coming year, I’m excited to share that Allie will be joining as a co-organizer, planning and leading events alongside me. In addition to hikes, we’ll be offering other social gatherings throughout the year — creating even more opportunities to connect, laugh, and build community off the trail as well.
💚 About contributions:
Maintaining this Meetup group comes with an annual cost of $560. While I do not require a membership fee, contributions are deeply appreciated to help offset these expenses. If you’re able to support the group, you can contribute:
- $15 for the year, or
- $3 per event
Contributions can be made in cash at an event or via Venmo at @Jacqueline-Ross-39. Your support truly helps keep this community going.
We hope you’ll join us — whether for a hike, a social event, or both — and help make 2026 a year of connection, movement, and fun. 🌈🥾✨
Upcoming events
3
🌈 Boston Pride & Esme Block Party Adventure! 🌈
Location not specified yet🌈 Boston Pride & Esme Block Party Adventure! 🌈
Hi everyone — Jackie here!
Yesterday Nancy and I headed into Boston for a Red Sox game at Fenway, and while we were there I had one clear thought: I am going to Boston Pride this year!
For those who don’t know my story — I moved to Boston in 1986 at age 19 to go to school, fell in love with the city, and especially fell in love with the gay/lesbian community and energy there. What was supposed to be school turned into a life chapter, and I stayed in and around Boston until 2019.
Since 1986, I’ve made it a tradition to attend either Boston Pride or NYC Pride every year. (And yes… NYC Pride is in a league of its own!) But Boston always knows how to bring the joy, celebration, and community spirit.
Since moving to Connecticut, I’ve enjoyed attending Middletown Pride and I deeply appreciate the folx who organize it. At the same time, many LGBTQ+ people I’ve met locally have shared that they’re craving more connection and community. So I thought… why not open the door and invite this group to experience Boston Pride together?### 🌈 The Plan (subject to fine-tuning as we get closer!)
- Leave early — around 7:00 AM
(If you know me, you know I believe in being early 😄) - Carpool depending on how many want to go
- Drive to Chestnut Hill/Brookline
- Park near the T station (approx. $3 for the day)
- Take the T into Boston — much easier than city parking!
- Arrive in Copley Square, where the main festivities happen
### 🎉 What We’ll Do
- Watch the Pride Parade (starts at 11:00 AM)
- Explore the festival with speakers, vendors, music, and celebration
- Head to the legendary Esme LGBTQ+ Womxn’s Block Party 💃🏽
Dancing, drinks, community, and pure fun
Tickets are usually around $15–$20 depending on when purchased.
### 🍜 Food?
Once we’ve had our fill of Pride magic, we can:
- Grab food in Boston (I know a great pho spot!)
- Or head back toward Chestnut Hill and stop somewhere on the way home
### 🏨 Overnight Option
If folx are interested, we can also discuss staying overnight at a hotel just outside the city in Newton and making even more of an adventure out of it. Let’s talk!
💜 Important Note
Everyone is welcome to join in whatever way feels right for you:- Stay with the group
- Branch off and do your own thing
- Meet up later
- Come for part of the day
Just please keep me posted so we know who’s doing what.
### 👟 Real Talk
This will be a long, FUN, joyful day with:
- Lots of walking
- Standing
- Crowds
- Music
- Dancing (if you choose!)
- And plenty of PRIDE 🌈
As we get closer, we’ll sort out all the details together.
### 🔗 Event Links
Boston Pride for the People:
https://www.bostonprideforthepeople.org/
Esme Block Party Tickets:
https://www.eventbrite.com/e/esme-lgbtq-womxns-block-party-pride-fest-tickets-1982978738788### ⚠️ Disclaimer
By choosing to attend, each person is responsible for their own transportation, decisions, safety, and participation. I assume no responsibility and waive any liability related to travel, attendance, or activities connected with this outing.
Who’s interested? 🌈✨5 attendees- Leave early — around 7:00 AM
Dinner and a Show -- Collective Rage
Marketplace, 7 North Street, Litchfield, CT, USHi folks, this is Allie. I'm going to be hosting some events for the Pathfinders and thought that a fun first would be a night out at the Goshen Playhouse on June 13. As you may know, the Playhouse is a favorite of Jackie's. In fact, she is going to be in the cast in an upcoming show. The show is Collective Rage: A Play in Five Betties. Jackie has the part of the narrator.
We’ll kick off the evening with dinner at The Marketplace Tavern in Litchfield Center at 6:00 pm sharp, then venture just 15 minutes down the road to the Goshen Playhouse for the show, which starts at 8:00pm. The Playhouse encourages attendees to bring snacks and drinks of all kinds to enjoy!
Tickets are $15 (plus service fees), and dinner will be on our own. You can buy tickets here. (Be sure to choose June 13.) I'm with a group of four and we have bought the seats at Table H. If you want, use the comments to tell people where you are seated and we can group together at the theatre.
You can also purchase tickets and just go to the show - your choice!
Here's a little bit about the show. (Full disclosure, this is an AI summary from the Internet.) It a story of five very different New York women, all named Betty. One is rich and bored, one a lonely 1950s-style housewife, one a Sephora employee aspiring to be a star, one a butch mechanic, and one a gender-nonconforming boxing gym owner. They work together on a new version of Pyramus and Thisbe, the play-within-a-play from A Midsummer Night's Dream.
As the women meet, fall in love, and rehearse, they shatter social norms and stereotypes that have long confined them, realizing they have been stuck reading the same scripts for too long.
The story is told in 19 short, TV-comedy-like scenes that end in a chaotic yet transformative production where the Betties learn to accept themselves and each other. The story is ribald and raucous, ultimately offering an upbeat and honest exploration of what it means to be a Betty in the modern world.
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