Most holiday seasons on the Yonge Street stretch between Rosedale and Summerhill stations come down to familiar addresses, and this one does too, with one exception. Shay Ristorante opened at 1055 Yonge St. in the fall, and it is the only new dinner room on the strip going into December. The other restaurant expected on this corner of Summerhill has moved its arrival to the summer of 2027. That leaves Shay's courtyard and private room as this season's newcomers. The rest of December's calendar comes from church sanctuaries along Yonge and a former brickyard at the bottom of the valley.
Together they cover a December that never leaves Rosedale: dinner on Yonge, carols up the street and Sundays down at the Brick Works.
The One New Room on the Strip
Streets of Toronto reported on September 30, 2026 that Shay would open on October 1 at 1055 Yonge St. Toronto Life profiled it on October 6, listing the owners as Justin Friedlich, Rayana Dilawri, Luli Lavdari and Adam Halpern, with Friedlich as chef.
The partnership started at the Buca in Yorkville. According to Toronto Life, Friedlich came up at Buca and rose to chef de cuisine. He met Dilawri and her family when they were regulars at the Yorkville location, and Lavdari, then Buca Yorkville's manager and now Shay's director of operations, brought the group together. Toronto Life said the pitch was to take their high-end restaurant backgrounds and build something "hospitable, homey and unpretentious."
Toronto Life's review describes the menu like this.
| Dish | What it is | Price |
|---|---|---|
| Salmon tartare | Ora King salmon, trout roe, lemon aïoli, house-made potato chips | $32 |
| West Coast scallops | Seared on the half shell, chive beurre blanc, dehydrated prosciutto | $39 |
| Ravioli di mare | Half squid-ink pasta, shrimp and scallop filling, shrimp-shell brodo | $42 |
| Tiramisù Nero | House-made chocolate ladyfingers, marsala, mascarpone cream | $18 |
| Babà al rum | Rum cake with stewed pears and mascarpone-vanilla cream | $18 |
Every meal starts with complimentary house focaccia and Sicilian olive oil. Toronto Life credits the recipe testing to Shay's pasta maker, Ledora Cegrani, who learned focaccia from her mother as a child.
The bar is the reason Shay matters to December planning. Halpern's wine list runs past 600 labels, and Toronto Life reported that bottle prices start in the hundreds and go well into the thousands. The by-the-glass list opened with about 50 choices and is expected to reach 100. The house negroni uses Dillon's dry gin infused with powdered sumac flowers and costs $18. The Oliveto, a gin sour finished with olive oil from an estate outside Palermo, costs $19.
A Private Room Sized for the Season
The room itself seats 90, with marble, velvet banquettes and warm millwork. A side courtyard adds a second place to settle in. The private dining room, La Sala, is the part that fits the season best. Shay's private dining page says La Sala holds up to 18 guests, with menus and timing arranged through the events team. Groups of nine or more can contact that team by email.
A family dinner of a dozen, a small office gathering or a party with out-of-town guests now has a room on Yonge sized for it, within walking distance of most of Rosedale. Shay takes reservations online and does not accept walk-ins, so December evenings need booking ahead. The same page offers e-gift cards and presents them as a holiday gift.
The Rest of the Calendar Belongs to Older Addresses
Once you leave Shay's dining room, the season belongs to institutions that have hosted it for a long time. These are the dates on the books for the weeks after this post goes up.
| Date | Event | Where |
|---|---|---|
| Sundays, Nov 29 to Dec 20 | Evergreen Winter Market, 11 a.m. to 5 p.m. | Evergreen Brick Works |
| Dec 1, 2 and 3, 7:30 p.m. | Toronto Mendelssohn Choir, Festival of Carols | Yorkminster Park Baptist Church, 1585 Yonge St. |
| Dec 8 | Christmas Carol Concert & Sing-Along | Rosedale United Church |
| Dec 17, 5:30 p.m. | Tidings of Comfort | Rosedale United Church |
| Dec 20, 11 a.m. to 5 p.m. | Public skate and Solstice Walk | Evergreen Brick Works |
Up Yonge, the Toronto Mendelssohn Choir brings its Festival of Carols to Yorkminster Park Baptist Church at 1585 Yonge St. for three evenings. The choir bills it as a carol sing-along with festive works, so the audience sings too.
Closer to home, Rosedale United Church holds its Christmas Carol Concert & Sing-Along on December 8. The program brings together the Metropolitan Silver Band, Music Director Dr. Sarah Svendsen and the church's Christmas Choir, and donations go to a local food bank. On December 17 the church holds Tidings of Comfort, a 5:30 p.m. service for people living with grief or loss during a season that can be hard to mark.
The carol nights fall on weeknights at 7:30 p.m. That timing makes an early dinner at 1055 Yonge followed by the Festival of Carols up the street an easy evening plan.
Down the Valley on Sundays
The weekend half of the season happens below the neighbourhood. The Evergreen Winter Market runs four Sundays at the Brick Works, November 29 and December 6, 13 and 20. The vintage and artisan market is open 11 a.m. to 5 p.m. each Sunday, with more than 90 vendors. Entry is pay-what-you-can, with Evergreen suggesting $5 per person or $20 per family.
Every Sunday also brings live local performers in the Winter Lounge, a food court of local vendors and the Art Hive, a free community art studio. The outdoor Winter Garden, with fire pits, s'mores and hot drinks, runs only on the first two Sundays, November 29 and December 6. The Evergreen Garden Market sells Christmas trees, which takes care of a Sunday errand on the same trip.
December 20 is the fullest day of the market. Weather permitting, Koerner Gardens opens for a public skate with rentals available, and visitors can make a lantern and join the Solstice Walk. Evergreen also runs festive workshops with partners such as Rooks to Cooks and Let's Make It. These sessions need registration, so book them before the Sunday you plan to go.
What Waits Until 2027
Next year's changes explain why this December has only one new room. Mamakas, the Greek restaurant expected in Summerhill, said in a blogTO report in November 2025 that it would open in 2026. Its own location page now says "Welcoming you Summer 2027." That puts the next big arrival on the strip at least two seasons away.
The valley has a longer timeline still. The City of Toronto's Rosedale Valley Road multi-use trail project covers the route between Bayview Avenue and Park Road. As of the page's May 2026 update, the City expects to tender the work in 2026 and begin construction in 2027. Those are the City's planned dates, and work this winter is not expected.
Until then, the neighbourhood's December is easy to map. It runs from a 90-seat room at 1055 Yonge to two church sanctuaries on Yonge, then down the valley to four Sundays at the Brick Works, ending with the skate and Solstice Walk on December 20.
At Barry Cohen Homes, we follow how new rooms like Shay and long-running traditions like these shape daily life in Rosedale. If you're thinking about what your Rosedale home is worth as the year closes, we'd welcome the chance to request a complimentary valuation or schedule a confidential consultation at a time that suits your holiday calendar.
