Best Anniversary Restaurants in Westport (2026)
Published · Updated
The 2026 Westport anniversary pick is The Cottage, chef Brian Lewis's weekly-changing room and a 2025 James Beard nominee. Editorial runners-up: Gabriele's, Casa Me, Rive Bistro, Rizzuto's, Allium Eatery.
Low light off warm wood, a fire going, plain linen and a menu that changed this week — the particular hush of a room that takes the night seriously. Seventeen Westport rooms sit in our directory; six carry an anniversary.
Six Westport Tables for an Anniversary
Brian Lewis changes the menu weekly at The Cottage on Post Road East, a converted space that reads like a well-kept New England parlour — low light, warm wood, quiet service. The sauteed foie gras with vanilla quince is the recurring luxury; Copps Island oysters with a yuzu-ginger mignonette open the night. Lewis is a 2025 James Beard nominee for Best Chef: Northeast. For an anniversary that wants the best kitchen in Fairfield County and a room built for two.
Gabriele's of Westport sits at 27 Powers Court beside the Country Playhouse, an Italian steakhouse where chef Dagoberto Turcios-Cruz ages prime beef 28 days and pours A5 Kobe alongside handmade pappardelle Bolognese. Dry-aged cuts run in the $50s and $60s. It is the celebratory, old-school room for an anniversary that wants steak and a wine list. For an anniversary that wants dry-aged beef and Italian warmth over a tasting menu.
Casa Me opened on a corner of Sconset Square at 7 Sconset Square in November 2022, in a former fashion designer's room, with Milanese chef Emiliano Miglionico rolling the pasta in-house. The mafaldine al limone and the pinsa romana are the orders; mains land in the high $20s and $30s. It is Westport's most polished Italian, intimate and softly lit. For an anniversary that wants a sleek Italian room and house-made pasta.
Rive Bistro occupies a converted building on Riverside Avenue where the Saugatuck River shows through the windows, and chef Eric Sierra cooks a French bistro in the full sense — dark wood floors, burgundy leather banquettes, a fireplace as the room's centrepiece. Entrees sit in the $30s and $40s. The river view makes every table feel like an occasion. For an anniversary that wants a proper French bistro and a fireside table by the water.
Rizzuto's sits at 540 Riverside Avenue over the Saugatuck River, an Italian-American room with a serious raw bar and wine program that, in its own words, handles a couple's anniversary with the same ease as a corporate table. Oysters, grass-fed steaks and wood-fired Neapolitan pizza fill it out, mostly in the $20s and $30s. For an anniversary that wants a river view, a raw bar and an easy, unfussy room rather than a hushed tasting.
Allium Eatery sits across from the Westport train station at 54 Railroad Place, where chef Michelle Greenfield — a 2025 James Beard semifinalist for Best Chef: Northeast — cooks a frequently-changing farm-to-table menu from Connecticut farms. The room is small and intimate, mains in the $30s and $40s. For an anniversary that wants a quiet, thoughtful seasonal dinner and a kitchen on a James Beard trajectory.
How to Book
The Cottage is the room to plan around — book a week or two ahead, especially for a weekend. Gabriele's, Casa Me and Allium take Resy or OpenTable tables a few days out; Rive Bistro and Rizzuto's hold river-view tables that go first on warm-weather weekends, so reserve those early.
A weekend evening suits an anniversary. Ask for a river-view table at Rive Bistro or Rizzuto's, a corner two-top at The Cottage or Allium, and a banquette at Casa Me.
Frequently Asked Questions
The 2026 editorial pick is The Cottage on Post Road East, where chef Brian Lewis — a 2025 James Beard nominee for Best Chef: Northeast — changes the menu weekly in a New England parlour room. For a celebratory steak dinner, Gabriele's Italian steakhouse on Powers Court; for the most polished Italian, Casa Me on Sconset Square.
Rive Bistro on Riverside Avenue is the most openly romantic — a French bistro with dark wood, burgundy leather banquettes and a fireplace, set where the Saugatuck River shows through the windows. The Cottage's low-lit parlour and Casa Me's softly-lit Italian room on Sconset Square are the close alternatives for a quiet anniversary for two.
It ranges from Casa Me, Rizzuto's, Rive Bistro and Allium in the high $20s through the $40s a plate, to Gabriele's dry-aged steaks in the $50s and $60s, and The Cottage at the top with its weekly-changing menu and foie gras. An anniversary lands comfortably in the $40-to-$70-a-head range at most of these.
The Cottage's Brian Lewis is a 2025 James Beard nominee and three-time semifinalist for Best Chef: Northeast, widely called the best kitchen in Fairfield County. Allium Eatery's Michelle Greenfield was a 2025 James Beard semifinalist in the same category, making both Railroad Place and Post Road East strong anniversary tables on the strength of the kitchen alone.
Book The Cottage a week or two ahead, especially for a weekend. Gabriele's, Casa Me and Allium take Resy or OpenTable tables a few days out. Rive Bistro and Rizzuto's hold river-view tables that fill first on warm-weather weekends, so reserve those early in the week for the best seat.