When it came to planning their wedding, Molly and Tom weren’t chasing a childhood dream or Pinterest-perfect vision. In fact, they’ll tell you straight up—they didn’t love wedding planning. But what they did love? Building the weekend together. Finding a rhythm as a team. And ultimately, creating a celebration that felt entirely true to who they are.
What started with PowerPoint presentations over dinner turned into a shared vision: something small, intentional, and grounded in quality time. They didn’t want just a party. They wanted a place where everyone could stay, eat well, dance hard, and just be together. Enter: a Chebeague Island Inn wedding.
Why Chebeague Island Inn Just Felt Right
Neither of them had been to Chebeague Island until their tasting (yep, bold move), but they were chasing a vibe, not a checklist. They always said they wanted a backyard wedding—just one bigger than their own—and Chebeague offered that in the most magical way.
Perched above Casco Bay with wraparound porches and the kind of charm that feels lived-in, the inn wasn’t just a venue—it became the heart of the whole weekend. Everyone could stay put, no cars or chaos, and just enjoy the rhythm of island life.
For Molly and Tom, it also brought things full circle. Years before, they had saved up for their first real vacation together—a trip to Maine that sparked a deep love for the coast. Getting married there? Pretty poetic.
Friday Ferry Rides and Dance Floor Magic
While the main event was packed with unforgettable moments—live music, epic food, nonstop dancing—it was a quiet moment before the ceremony that they’ll never forget.
After the rehearsal lunch in Portland, they hopped on the ferry back to the island. Sitting side by side, wind in their hair, they looked at each other and realized: the planning was done. They were officially in it. The excitement kicked in, the tension melted away, and they got to just be.
On wedding day, the energy was calm, connected, and full of love. Guests did morning yoga on the lawn, Tom golfed with friends, and Molly’s sisters created a glam station that doubled as a family hangout. Molly even sprinted outside in her pajamas to kiss Tom between holes—because why not?
And the dance floor? Wild. Every direction they looked, someone they adored was dancing, laughing, or crying happy tears. “Joy from every angle,” they said. The best kind of chaos.
Details That Felt Like Them
There was no strict color palette or formal dress code. The vibe was “fancy backyard dinner party” meets slightly-glam coastal Maine. Molly wore a secondhand dress. Guests were encouraged to shop their closets. Florals were wild and whimsical. And they even picked blooms from the inn’s garden for Molly’s bouquet that morning.
It wasn’t curated to perfection—it was curated to them. From signature cocktails to an enormous bottle of champagne-turned-guestbook, every element felt intentional and low-pressure.
Advice From the Couple
- Know your priorities. For Molly and Tom, it was food, music, and making people feel taken care of.
- Don’t be afraid to break the “rules.” This wedding skipped a lot of traditions and gained a lot of heart.
- Find vendors who feel like friends. Their team didn’t just deliver—they helped shape the experience.
- Plan with your strengths. Tom brought the big-picture ideas. Molly brought them to life.
Venue: Chebeague Island Inn | Photography: Gabby Riggieri Photography | Videography: Justin Reath | Florals: Clo Floral | Band: Kahootz Entertainment | Planning: Casey, Coastline Weddings | Catering: CII/58 Culinary | Cake/Dessert: Two Fat Cats | Rentals: One Stop, BBJ Linens | Transportation: Fogg’s Water Taxi
Thinking About Your Own Chebeague Island Inn Wedding?
If you’re dreaming of a weekend where your people feel like family, where every moment is full of meaning, and where the coast of Maine wraps you up in its magic—this might be your spot. A Chebeague Island Inn wedding isn’t just beautiful, it’s grounding, welcoming, and deeply personal.
Looking to feature your Maine wedding in Evergreen Weddings Magazine? Reach out—we’d love to hear your story.
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