Write With Jenny

Upcoming Trips & Classes

Writing and Renewal in Maine’s North Woods
With Adventures in Good Company
August 5 – August 10, 2023

Escape to a lakeside writing retreat in the iconic landscape of Maine’s north woods, defined by their solitude, sparkling lakes, and incredible wildlife. Spark creativity as you engage your body in the outdoors. Discover the stories you want to tell as you learn new skills, expand your comfort zone, and cultivate an awareness of the natural world. Then, with the encouragement and instruction of AGC guide and professional outdoor writer, Jenny O’Connell, craft your stories into pieces of writing you’re proud of. Explore this beautiful corner of the country by foot, kayak, and raft, and return each night to comfortable green built lodges nestled amongst the pines on Millinocket Lake. All genres and writing levels are welcome! On our last night, we’ll share our work out loud and celebrate together in the company of our supportive group.

Hurricane Island Outward Bound School Writers Expedition (Waitlist only)
August 13 – August 19, 2023
Ages 14-16

The Telling Room and Hurricane Island Outward Bound School (HIOBS) are excited to offer this unique collaborative “Writers Expedition” for only $700, thanks to generous philanthropic support from The Whitehead Foundation.

Participants will spend five days canoeing the wild blue waters of the Rangeley Lakes area, sleeping under the stars, searching for wildlife, learning camping and canoeing skills, building friendships with fellow writers, and crafting pieces of writing inspired by the adventures they have along the way. This expedition will depart from HIOBS’s mountain base in Newry, ME. Participants will benefit from both nonprofits’ expertise in youth leadership and empowerment. Scholarships are available! 

100 Mile Wilderness Backpacking and Creative Writing Adventure
September 1 – September 8, 2023

Considered one of the wildest sections of the Appalachian Trail, the 100 Mile Wilderness spans from Monson to Millinocket, ME. On this 7-day trek led by two experienced guides, you’ll section hike across 52 miles of wild lakes, sweeping mountain views, mossy forests, and remote, rugged terrain. Summit Whitecap Mountain, dip in freezing lakes, watch for shooting stars, and enjoy the raucous laughter and company of new friends. You might even witness trail magic, or a moose sighting! With time built in for guided yoga and writing sessions to deepen your experience, each night you’ll feel the sense of accomplishment that comes from pushing your body, mind, and spirit in the wilderness.

This trip is for backpacking enthusiasts who want to safely increase their level of challenge in a supportive environment, and creative folks who are interested in exploring writing as a tool for reflection, expression, and compelling outdoor storytelling.

Writing the Creative Magazine Feature
Maine Media Workshops + College
September 25 – September 29, 2023

In this five-day intensive, you’ll uncover the stories you want to tell, and learn how to take one of those stories from brainstorming to publication. Through an exploration of creative writing techniques such as sensory writing, setting, character, and dialogue, you’ll hone the tools that bring stories to life. Guided by Jenny’s expertise in experiential education, you’ll walk the Rockland Breakwater to practice setting and hook writing, and conduct peer interviews aimed at wholehearted characterization and locating the “heat” in dialogue. At the end of the week, you’ll leave with a developed story, polished with peer feedback, and a solid idea of the next steps for pitching it for publication. One-on-one meetings with the instructor are available.

Writing Services

What draws me most to creative writing is the potential it allows for connecting people to each other, to the world, and to the experience of being alive. I come to my mentor sessions with 14 years of teaching experience, eight years as a professional writer, and a creative arsenal of tools to help you generate new creative material, hone your craft, and prepare your writing for publication. I would love to walk with you on your writing journey!

Creative Writing Warm-Up: Get the creative juices flowing, generate new work, and set up structures for success in your writing. I will guide you through a series of custom-tailored prompts aimed at unlocking the stories you want to tell, work with you to establish and stick to a writing routine, help you curate a reading list relevant to your writing, and provide a phone consultation with feedback on your writing samples. This is a great option for writers looking to develop a new body of work quickly. 

Manuscript Critiques: This option is for work (personal essays, memoir excerpts, or short nonfiction) that is ready for the revision process. I will read up to 25 pages of your writing with a focus on voice, setting, vulnerability and interior, characterization, and structure, as well as other elements that need attention. You will receive a detailed letter with feedback, as well as suggestions for deepening the work, and if desired, placing it with a publication.

Custom Mentorship: This is a flexible option for those looking to improve their creative nonfiction writing over the course of a few months or longer, or for writers looking for developmental edits on a longer body of work. This service is customized to the individual, and depends on the writer’s goals and needs. 

Group workshops: Give your friends and/or co-workers the gift of creativity! Through custom-tailored workshops, we’ll generate creative material, hone our craft and storytelling skills, and practice sharing our work with each other. For groups of six or more.

The Wilderness Within: An outdoor guide for 13 years, I offer sea kayaking, backpacking, and hiking expeditions aimed at connecting to our creative courage through pushing the limits of our bodies in the outdoors. Each experience is crafted to include a balance of learning technical skills, exploring the outdoors, and writing time. Custom expeditions (rock climbing, ice climbing, winter camping, whitewater rafting or canoeing, and international travel) are subject to the availability of additional guide team members, but may be available upon request. 



Jenny is able to create a special magic in her classes: a product of both her multitude natural gifts and her finely-honed teaching craft. She creates a warm, loving, deeply personal container which, when combined with the varied structure and thoughtfully curated prompts and themes, really lays a potent ground for magic to arise. I did some of my best writing in years with Jenny. She helped me discover abilities and insights I didn’t know I had.

Mira Manickam, San Francisco, CA

Jenny has a way of helping me get out of my own way. Through her coaching and guidance, I was able to push aside the judge that camps out in my head, and write freely and authentically. She helps me write in my own voice.

Johanna Sorrell, New Hampshire

“I loved it all! Jenny’s invitations were really sweet and thoughtful and definitely made my experience above and beyond. Even just a little feedback from her really gets my gears turning on ways to make my writing better and closer to what I am trying to say.

Amanda Gavin, Portland, Maine

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