The Monroe Sun's Restaurant Week feature counted 25 restaurants, delis and coffee shops for the October 10 through 17 run. Eleven of them have addresses between 415 and 650 Main Street. That is the Stepney stretch of Route 25, a walk of well under a mile from Vazzy's Osteria to MacDaddy's.
Monroe has no single downtown, and Restaurant Week covers the whole town. Its roster still lands in four clusters along two state roads, plus one drive-in up by the lake. The clusters aren't the same size, and they aren't changing at the same speed.
Four clusters, one of them carrying the weight
This is where the Monroe Sun's 25 participants sit, grouped by corridor.
| Corridor | Address range | Participants | Who's there |
|---|---|---|---|
| Stepney, Main St./Route 25 | 415 to 650 Main St. | 11 | Vazzy's Osteria, Country Pizza, Last Drop Coffee Shop, Takumi Ramen & Grill, Thai Mi Noodle, Monroe Fish Market, Monroe Social, Testo's, Monroe Diner, Honeyspot Pizza 5, MacDaddy's Macaroni & Cheese Bar |
| Lower Main St. | 89 to 262 Main St. | 6 | Osteria Romana, El Gallo De Oro, Nonna's Pizza & Pasta, Terra Café, El Sol Deli, Flames |
| Monroe Turnpike/Route 111 | 380 to 500 Monroe Tpke. | 5 | Jennie's Pizzeria, Aldini's Restaurant and Pizzeria, Bill's Drive-In, J1 Sushi & Japanese Kitchen, Bella Rosa Ristorante |
| Tollgate Plaza | 838 Main St. | 2 | Mr. Mac's Canteen, Mama Rosa Restaurant |
| Route 34 | 14 Roosevelt Dr. | 1 | Lake Zoar Drive-In |
The town's official Restaurant Week page lists 23 participants. Thai Mi Noodle and Terra Café appear in the Monroe Sun's coverage but not on the town's list. Even on the town's shorter list, Stepney still has more participants than any other corridor.
Stepney filled in one storefront at a time
The Stepney cluster didn't open all at once. It built up over close to five decades, and the dates are right there in the Monroe Sun's profiles.
- 1978: Country Pizza & Restaurant took the corner of Pepper and Main at 418 Main St. Owner Andy Vasiliou told the Sun the sausage pie is still the top seller.
- 2004: Vazzy's Osteria opened at 415 Main St.
- December 2012: The building at 568 Main St. reopened as the Monroe Diner, following the long run of the New Colony Diner.
- November 2016: Monroe Social opened at 494 Main St. Next month makes ten years.
- About 2024: Ralph Giacobbe came out of a brief retirement to open Testo's at 505 Main St. with his family. The restaurant traces back to the original Testo's his uncle, Mario Testa, opened on Madison Avenue in Bridgeport in 1976.
- November 2024: Takumi Ramen & Grill held its soft opening and ribbon cutting at Stepney Crossing, 435 Main St. Owner Alan Yang spent 20 years as a hibachi chef at his brother's restaurants in Mississippi before opening his own place here.
Takumi shares Stepney Crossing with Last Drop Coffee Shop. The Monroe Sun describes Last Drop as usually packed at breakfast and lunch. With a coffee shop, a ramen and hibachi kitchen, Thai, seafood, a diner and red-sauce Italian on the same stretch, Stepney covers more meals of the day than any other cluster on the list.
Monroe Social's owner, Constantin Crama, described what Restaurant Week does for a place like his to the Monroe Sun:
"It brings in a lot of people. Otherwise, you wouldn't see some of these people. They travel from all over. I'm excited to see these new faces."
His regulars have a reason to come back after the week ends. Monroe Social runs a Sunday night deal with a 12-ounce New York strip for $20 and a half-price bottle of wine, according to the same story.
Route 111 is where the oldest names are
Stepney has the most stops, but the oldest names on the roster are out on Monroe Turnpike. Bill's Drive-In at 431 Monroe Turnpike dates to 1942. It started as Ligouri's Drive-In before William "Bill" Boyko bought it, and it has changed hands twice since then. Jennie's Pizzeria at 380 Monroe Turnpike is older still. It opened in Bridgeport 90 years ago and has been in Monroe since 1999, and the Sun calls it the oldest pizzeria in Fairfield County. Brothers Al and Richard DeSimone run it, and Richard told the Sun the No. 1, their "super works" pie, is the specialty.
The Turnpike cluster is organized by plaza. Aldini's is in Village Square at 401, and Bella Rosa Ristorante is in Gaslight Square at 500. Bella Rosa owner Dave Rodrigues, who has lived in town since 1982, opened in 2011 and is known for Portuguese dishes such as Shrimp Mozambique alongside the Italian menu. J1 Sushi took over the former Dunkin' Donuts space at 447 Monroe Turnpike after a renovation that co-owner Lynn Chen said took almost a year.
On Route 111, new places mostly move into existing plaza and pad spaces. On Stepney's Main Street, the storefronts themselves are changing hands. That second pattern explains what's happening at Stepney now.
Lower Main is where Restaurant Week got started
The six stops at the south end of Main Street have a claim on Restaurant Week itself. Jaime Zuniga, one of the owners of Osteria Romana at 89 Main St., told the Monroe Sun he suggested the idea to Terry Rooney when he first came to town, before Rooney was first selectman, "and he and others were very supportive of it." This year Osteria Romana ran its own "Italian Passport" inside the town's passport, organized by regions of Italy.
This stretch also has some of the menus that are hardest to find elsewhere in town. Terra Café at 150 Main St. was founded by two Azoreans and stocks Portuguese and Azorean cheeses, tinned fish and sweets next to its breakfast menu. El Sol Deli at 179 Main St. is owner Javier Rangel's third location, and he calls his family "the creators of the taco empanada." Nonna's Pizza & Pasta at 140 Main St. and Flames at 262 Main St. fill out the cluster.
At the other end of town, Tollgate Plaza at 838 Main St. pairs Mr. Mac's Canteen and its chili dog with Mama Rosa's Mexican menu. Lake Zoar Drive-In on Route 34 has been serving the Zoar Burger since 1993.
The next changes are landing in Stepney
The stretch with the most restaurants is also the one with the most going on this fall.
The Rite Aid space is getting a new tenant. Rite Aid's Stepney Crossing store closed as part of the chain's national closings, which the Monroe Sun reported in July 2025. The Monroe Turnpike store at 508 closed too, and in June the Planning and Zoning Commission approved Town Fair Tire's plan to move into that building, the Monroe Sun reported. According to the Monroe Sun's October 7 report, Aubuchon Hardware plans to move from 590 Main St. into that space. Its site plan asks for an outdoor propane filling station and a fenced seasonal display area. Those would use eight of the plaza's 198 parking spaces, so the application also requests a shared-parking reduction. Plaza owner David Sippin told the commission that because businesses at Stepney Crossing keep different hours, parking is always available. The commission was expected to vote at its October 15 meeting, and the article gave no move date. Once the move happens, the coffee shop, the ramen counter and the hardware store will all share one parking lot.
A new shop is opening across the street. Hyacinth Consignment Boutique at 446 Main St. sells clothing, shoes, bags and jewelry. The Monroe Chamber scheduled its ribbon cutting for October 21.
A restaurant is expected farther up Route 25. In August, the Planning and Zoning Commission unanimously approved a three-story mixed-use building at 715 Main St. The plan has 20 one-bedroom apartments over about 8,720 square feet of commercial space split into three units. Developer Stephen Shapiro told the Connecticut Post a restaurant was already expected in one of those units. No tenant has been named.
The passport deadline and what's next on the calendar
Collect stamps from three different participating businesses and your passport is complete. Turn it in to the Economic Development Department at Town Hall during business hours by Friday, October 23, while the Monroe tote bags last. The rules are on the town's Restaurant Week page.
After that, the local calendar moves to smaller rooms. Harmony Grange No. 92 at 103 Hurd Ave. has these events listed:
- Beginners Mandala Painting Workshop, Sunday, Oct. 25, 3 to 5 p.m.
- Charcuterie and Wine with This N That Catering, Saturday, Nov. 7, 7 to 9 p.m.
- Beginner Needle Felting Workshop with Needle Felted Fuzzies, Saturday, Nov. 14, 2 to 4 p.m.
- Holiday Sip and Shop and Festival of Trees, Dec. 4 and 5
The Monroe Chamber's calendar lists SchmoozaPalooza 2.6 on Oct. 28, a Newtown Savings Bank Shred Day on Oct. 31, and "A Toast to November: Wine Tasting Event" on Nov. 4.
If you live in Monroe and want to talk through what your own corner of town is worth, from Stepney to the Turnpike to up by Lake Zoar, the Grasso Team is glad to help. We follow these Main Street changes closely, and you can start with a home valuation or browse our Monroe neighborhood page. Contact Us anytime.
