Walk into 319 Main Street this month and you'll find teal and orange paint, comic-book pages laminated under the tabletops, and a menu built around a burger called the Rattle Burger and thirteen kinds of milkshake. Rattle Shake Grill opened here this spring, the second location for the South Portland burger spot, and co-owners Matt Moran and Michael Gatlin brought in Tobey Moulton to run the front of house. Moulton knows the building. He used to own it.
That's the detail that makes this address worth a second look. Before Rattle Shake Grill, 319 Main Street was Rise Pizza & Pub, which Moulton opened in August 2023. Before Rise, it was Louie's Grille, a spot Cumberland diners had counted on for close to a decade before it closed. Three restaurants, one door, roughly a dozen years. Across town on Gray Road, Mère opened its doors for the first time ever on September 26, in a building that had never served a customer before this month. Cumberland's two commercial streets are growing in opposite directions this fall, and the same week makes the contrast easy to see: the Cumberland Fair, in its 154th year, opens right alongside both of them.
The Address That Keeps Changing Its Mind
Louie's Grille was the kind of place regulars call a staple without needing to explain why. Owner Jim Guidi closed it in 2023, a change significant enough that The Forecaster covered it as local news. Moulton and chef Rocco Marzilli bought the building that summer and opened Rise Pizza & Pub weeks later, betting that the space still had a restaurant in it.
Rise ran for about two years before closing in 2025. Moran and Gatlin, who'd already built one Rattle Shake Grill on Cottage Road in South Portland, saw an opportunity in the empty building and in Moulton's standing in the community. Moran has said the businesses likely wouldn't have come to Cumberland without Moulton's involvement, since he brings the kind of familiarity that makes a new sign feel less like a gamble to regulars walking by. The renovation kept things light: new paint, new upholstery, the same bones.
| Name | Approximate Run | Notable Detail |
|---|---|---|
| Louie's Grille | roughly 2013–2023 | described as a decade-long neighborhood staple before closing |
| Rise Pizza & Pub | August 2023–2025 | opened by Tobey Moulton and chef Rocco Marzilli |
| Rattle Shake Grill | spring 2026–present | second location of the South Portland burger and shake spot, with Moulton running front of house |
Three names, one storefront, and the fastest of the three turnovers happened in under three years. Whatever else is true about Cumberland's Main Street, it isn't short on appetite for a new restaurant in a familiar spot.
A Building With No Restaurant History to Inherit
Gray Road tells a different story. The building at 204 Gray Road sold for $700,000 in June 2026, a general-purpose commercial shell zoned for uses ranging from professional office to daycare to restaurant, with high ceilings, two large open spaces, and parking for fifteen or more vehicles. Nobody had run a kitchen out of it before. Pastry chef Georgia Macon and her team built one from scratch, and Mère opened as a from-the-ground-up concept rather than a reopening.
Macon's résumé is the kind that gets a bakery covered before it has a sign up. She trained at Le Cordon Bleu in Paris, worked in St. Louis, and spent time at Tartine Bakery in San Francisco before landing in Maine as executive pastry chef for the Prentice Hospitality Group, where her work at Twelve earned coverage in Boston magazine, The New York Times, and The Wall Street Journal. StarChefs named her a Rising Star pastry chef in 2023. Mère's menu leans on naturally leavened breads and pastries alongside take-and-bake dinners like chicken pot pie, slab pizza, and shepherd's pie, plus a small market stocked with cheeses, cured meats, preserves, and Maine-made goods. The shop runs seven days a week from 7 a.m. to 7 p.m. Macon has said Cumberland seemed like it really needed something like this, and the roughly three months between the project's announcement in June and its opening in late September suggest she wasn't alone in thinking so.
Gray Road wasn't empty ground before Mère arrived. Cumberland House of Pizza has run out of 176 Gray Road for more than two decades, the kind of tenure that makes it a fixture rather than a headline. The corridor has also picked up heavier investment in recent years, including a new headquarters building for the engineering firm Casco Systems at 197 Gray Road. Where Main Street reuses the same footprint under new management, Gray Road has been adding square footage that didn't exist before.
The One Thing on the Calendar That Hasn't Moved in 150 Years
Both openings land in the same week as the Cumberland Fair, which runs September 27 through October 3 at the Cumberland Fairgrounds on Blanchard Road, with harness racing continuing on October 4. This is the fair's 154th year. It started as the Cumberland Town Fair in the late 1860s, a two-day gathering where farmers showed produce and horsemen raced down Main Street, and it's been run almost without interruption since by the Cumberland Farmers' Club, the nonprofit that still organizes it today.
The fair draws more than 50,000 visitors over its run, and the entertainment lineup hasn't drifted far from its roots: the All-American Rodeo on Wednesday and Thursday evenings, daily harness racing, the Maine State Pumpkin & Squash Weigh-Off, a demolition derby to close things out, and the pig and calf scrambles that have been part of the program for generations. Gates open at 8 a.m., exhibition halls run 9 a.m. to 9 p.m., and admission is $15 a day for anyone 13 and older, with kids 12 and under free.
Everything else in town this fall is new or renamed. The fairgrounds are the one place on the map that would look familiar to a Cumberland resident from a century ago.
A Week Worth Planning Around
If you're mapping out the next few days, the town's two food stories and its oldest tradition all fit inside driving distance of each other:
- Rattle Shake Grill, 319 Main St., for the Rattle Burger or a milkshake in a room that still has Rise's old bones under new paint
- Mère, 204 Gray Road, open daily 7 a.m. to 7 p.m., for a naturally leavened loaf or a take-and-bake dinner to end the fair day
- The Cumberland Fair, 197 Blanchard Road, September 27 through October 3, gates at 8 a.m., for the pumpkin weigh-off and the rodeo evenings
- Cumberland House of Pizza, 176 Gray Road, the corridor's longest-running name, if you want a meal that isn't part of this year's news
Whichever road you take out of the village this week, something on it opened for the first time in years, and something else has been running since before anyone reading this was born.
If you're spending fair week comparing notes on what's new along Gray Road and Main Street, or you just want to talk about what Cumberland looks like from the ground up these days, Ana T.L. Dierkhising would love to hear where you ate first. Let's Connect.
