Why I Started Chatham Coffee Tour: Stories, Community & Life in Chatham

From Wall Street to Main Street Mahjong: Meet Jill Boudreau

What happens when a successful real estate professional decides to leave her comfort zone and hike 2,200 miles across America? In this episode of Chatham Coffee Tour, Barb Garside sits down with entrepreneur and adventurer Jill Boudreau to discuss her remarkable journey from banking and real estate to Appalachian Trail thru-hiker and founder of Main Street Mahjong. Jill shares memories of growing up visiting Chatham, why Cape Cod became a second home for her family, and how a simple search for mahjong tiles inspired the launch of one of Chatham’s newest small businesses. The conversation explores the lessons she learned on the Appalachian Trail, the growing popularity of mahjong, and how community, connection, and lifelong curiosity continue to shape her next chapter. If you love stories about entrepreneurship, reinvention, adventure, and Cape Cod living, this episode is a must-listen. 🎧 Hosted by: Barb Garside 🎤 Guest: Jill Boudreau Jill Boudreau is a longtime Chatham summer resident, entrepreneur, former banking executive, Columbia MBA graduate, and founder of Main Street Mahjong. She completed a solo thru-hike of the Appalachian Trail and continues to inspire others through her willingness to embrace new challenges and adventures. 💡 What You’ll Learn: ✔️ How Chatham became a second home for Jill and her family ✔️ What inspired her Appalachian Trail thru-hike ✔️ Lessons learned from living unplugged for five months ✔️ How Main Street Mahjong came to life ✔️ Why mahjong has become such a popular social activity ✔️ The importance of supporting local businesses ✔️ Favorite places to relax and recharge in Chatham 🎙 Connect with Jill: 🌐 Website → https://mainstreetmahjong.com/ [https://mainstreetmahjong.com/] 📷 Instagram → https://www.instagram.com/jillaboudreau/ 🔗 LinkedIn → https://www.linkedin.com/in/wellesleyluxuryrealestate/ 🎙 Connect with Barb: 🌐 Website → https://barbaragarside.exprealty.com/ [https://barbaragarside.exprealty.com/] 🔖 Don’t forget to LIKE 👍, SUBSCRIBE 🔔 and leave a COMMENT 💬 below.

From Chatham to the World & Back Again: Meet Lindsay Bierwirth

What makes Chatham feel like home — even after traveling the world? In this episode of Chatham Coffee Tour, Barb Garside talks with entrepreneur and educator Lindsay Bierwirth about growing up in Chatham, exploring the world through travel and teaching, and eventually returning to Cape Cod to build a life centered around family and community. Lindsay shares stories from her years abroad, working internationally through college, and her transition from teaching Spanish to launching Chatham Works alongside her husband Fred. Together, they built a wellness and coworking space designed specifically to support year-round Cape Cod residents and local businesses. The conversation also explores Lindsay’s personal health journey, including her experiences with stomach cancer and breast cancer, and how organizations like Cape Wellness Collaborative helped support her through recovery. If you love stories about entrepreneurship, resilience, wellness, and Cape Cod community life, this episode is a must-listen. 🎧 Hosted by: Barb Garside 🎤 Guest: Lindsay Bierwirth Lindsay Garre Bierwirth is a Chatham native and former educator with degrees from Hobart & William Smith College and Boston College. A three-time Boston Marathon finisher and two-time cancer survivor, she is an active volunteer with the Cape Wellness Collaborative and supports local initiatives for young families. 💡 What You’ll Learn: ✔️ What year-round life in Chatham was like growing up ✔️ How international travel shaped Lindsay’s perspective ✔️ Why Chatham Works focuses on community wellness ✔️ The realities of running a year-round Cape business ✔️ How Cape Wellness Collaborative supports cancer patients ✔️ The evolution of schools and diversity in Chatham ✔️ Favorite peaceful places around town 🎙 Connect with Lindsay: 🌐 Website → https://chathamworks.com/ [https://chathamworks.com/] 📷 Instagram → https://www.instagram.com/chathamworks/ [https://www.instagram.com/chathamworks/] 🎙 Connect with Barb: 🌐 Website → https://barbaragarside.exprealty.com/ [https://barbaragarside.exprealty.com/] 🔖 Don’t forget to LIKE 👍, SUBSCRIBE 🔔 and leave a COMMENT 💬 below.

Blooms, Books, & Cape Cod Living: Meet Connie LaMotte

Living in Chatham year-round is a unique experience—one filled with quiet winters, bustling summers, and a tight-knit community. In this episode of Chatham Coffee Tour, Barb Garside talks with her niece and Chatham local, Connie LaMotte, about building a life and business on Cape Cod. Connie shares the inspiration behind her new business, Wilderwood Florals, which provides beautiful, classic Cape Cod floral subscriptions to summer houses and vacationers. She also dives into her love for books, working at a local independent bookstore, and finding community during the quiet winter months. The conversation highlights Connie’s incredible resilience as she discusses managing a rare blood condition, aplastic anemia, while simultaneously training for and crushing the four-day Disney Dopey Marathon Challenge. They also touch on the very real issue of local housing and what it takes for young families to stay on the Cape. If you love Cape Cod living, fresh flowers, or stories of personal resilience, this episode is for you. 🎧 Hosted by: Barb Garside 🎤 Guest: Connie LaMotte 💡 What You’ll Learn: ✔️ How a seasonal floral subscription service works ✔️ Why blue hydrangeas are the ultimate Cape Cod flower ✔️ The reality of the Chatham year-round housing market ✔️ How Connie completed a 4-day marathon challenge ✔️ Navigating life with aplastic anemia on the Cape ✔️ The best winter activities for Cape locals ✔️ Where to find the most peaceful views in Chatham 🎙 Connect with Connie: 📷 Instagram → https://www.instagram.com/wilderwoodflorals/ [https://www.instagram.com/wilderwoodflorals/] 🎙 Connect with Barb: 🌐 Website → https://barbaragarside.exprealty.com/ [https://barbaragarside.exprealty.com/] 🔖 Don’t forget to LIKE 👍, SUBSCRIBE 🔔 and leave a COMMENT 💬 below.

Painting Cape Cod: Art, Ocean Inspiration & Creative Life in Chatham

Inspiration is everywhere on Cape Cod — from shifting tides and glowing sunsets to quiet winter marshes and hidden beaches. In this episode of Chatham Coffee Tour, Barb Garside talks with artist Whitney Heavey about her creative process, coastal inspiration, and life as a working artist in Chatham. Whitney shares how years of sketching, painting, and observing nature have shaped her signature style filled with vibrant blues, ocean movement, and expressive coastal landscapes. She explains how videos, sketchbooks, and changing seasons help fuel her creativity, and why embracing imperfection is an important part of being an artist. The conversation also explores Chatham’s winter beauty, favorite hidden local spots, renovating a Cape cottage, boating around Monomoy, and Whitney’s fascinating family ties to the historic SS United States ocean liner. If you love coastal art, Cape Cod living, creativity, or stories about building a meaningful life through art, this episode is for you. 🎧 Hosted by: Barb Garside 🎤 Guest: Whitney Heavey 💡 What You’ll Learn: ✔️ How Cape Cod landscapes inspire art ✔️ Why artists use sketchbooks and visual references ✔️ The importance of experimentation in creativity ✔️ How Whitney balances critique with artistic freedom ✔️ The emotional side of painting landscapes ✔️ Favorite beaches and hidden Cape Cod spots ✔️ What it’s like living year-round in Chatham ✔️ The connection between art and nature 🎙 Connect with Whitney: 🌐 Website → https://www.whitneyheavey.com/ 📷 Instagram → https://www.instagram.com/whitney_heavey_art/ 📘 Facebook → https://www.facebook.com/whitneyheaveyart/ 🎙 Connect with Barb: 🌐 Website → https://barbaragarside.exprealty.com/ 🔖 Don’t forget to LIKE 👍, SUBSCRIBE 🔔 and leave a COMMENT 💬 below.

Preserving Chatham’s History: Historic Homes, Restoration & Coastal Living

Historic homes tell stories — but preserving them takes vision, patience, and passion. In this episode of Chatham Coffee Tour, Barb Garside talks with Inga Walker about her journey into historic preservation, restoration, and real estate in Chatham. After years of vacationing on Cape Cod with her family, Inga eventually made Chatham her full-time home and began restoring a historic 1928 cottage. Her love for preservation eventually led her to launch Bar Cliff Home, a restoration and vintage design business focused on reclaimed furniture and historic character. Inga also shares the work she’s done preserving historic properties in Ohio, including helping raise $1.5 million to save one of the region’s oldest homes. The conversation explores how preservation intersects with real estate, why older homes can overwhelm buyers, and how thoughtful restoration can protect the character of a community. From hidden beaches and sailing to local events like the Christmas Stroll, this episode captures the lifestyle, creativity, and community spirit that define life in Chatham. 🎧 Hosted by: Barb Garside🎤 Guest: Inga Walker 💡 What You’ll Learn:✔️ How historic preservation impacts communities✔️ The realities of owning a historic home✔️ Why restoration requires creativity and patience✔️ How Inga built Bar Cliff Home✔️ Challenges buyers face with older properties✔️ What makes Chatham special year-round✔️ Favorite local spots around Cape Cod✔️ The connection between history, design, and real estate 🎙 Connect with Inga: 🌎 Website → https://www.ingaelizabeth.com/ 🔗 LinkedIn → https://www.linkedin.com/in/inga-walker-870aa429a/ 📷 Instagram → https://www.instagram.com/ingaelizabethdesigns/ 🎙 Connect with Barb:🌐 Website → https://barbaragarside.exprealty.com/ 🔖 Don’t forget to LIKE 👍, SUBSCRIBE 🔔 and leave a COMMENT 💬 below.