Festive Restaurants for the Holiday Season! - Stamford Moms

Are you looking for festive restaurants for your holiday meal with family or friends?
Whether you’re looking for a casual breakfast or fancy dinner, scroll down for options!

Stamford Downtown is hosting its 15th annual storefront façade decorating contest called “Deck the Downtown.” This year’s event features 25 Stamford Downtown businesses. Vote for your two favorites by casting a vote online through Wednesday, December 24 at 5 p.m. using this link! All voters will be automatically entered to win a $100 Stamford Downtown Card. Two cash prizes of $700 each will be awarded to the businesses. One for Best of Show in the Restaurant category and the second in the Retail/Service category.

Sign of the Whale

6 Harbor Point Road, Stamford
Enjoy a pop-up Christmas experience at Sign of the Whale!
Click here to make a reservation!

Brennan’s by the Beach

82 Iroquois Road, Stamford
Brennan’s by the Beach serves food daily from 11 a.m. – 9:30 p.m. and their decor is fun for the holiday season every year!

Mulino’s of Westchester

99 Court Street, White Plains, NY
Mulino’s of Westchester is perfection at every time of the year, but even more during the holiday season! Santa’s workshop is a must see year after year and a great reason to get the whole family dressed up. The restaurant is decorated through February and serves delicious Italian food for lunch and dinner.
You will absolutely want (and need) to make a reservation in advance!

The Americano

261 Main Street, Stamford
The Americano is decked out for the holidays. Serving contemporary American fare and craft cocktails it’s sure to get you in the holiday spirit!

Prime Stamford

78 Southfield Avenue, Stamford
Winter Wonderland on the Waterfront, anchored by the debut of its large-scale gingerbread house installations is on display at Prime Stamford! Enjoy a gingerbread-themed cocktail crafted with warm seasonal spice, signature gingerbread dessert highlighting classic holiday flavors, cozy Sunday brunch feature inspired by winter mornings on the water.

Crust Issues

Crust Issues in Norwalk is glowing for the holiday season! They are also offering a $40 seven-course tasting menu with complimentary beer + wine, Wednesday–Sunday. Dessert included.

The Stamford Diner

Enjoy breakfast, lunch or dinner at The Stamford Diner and enjoy their holiday themed scenes along with a Snow Globe Specialty Cocktail!

The Stillery

The Stillery has great holiday decorations inside, on the covered patio and outside!

The Royal Green

The Royal Green is located at Sterling Farms and is beautifully decorated both outside and inside… plus the food is delicious!

Lucky’s Classic Burger & Malt Shop

Lucky’s Classic Burger & Malt Shop has fun decorations and festive milkshakes to got with them!

If you’re looking to take a little road trip, Cava Restaurant in Southington is beautifully decorated this time of year!

If you’re looking for festive treats… Elm Street Diner in Stamford is the place to go for fun milkshakes!

Enjoy a Meal with Santa

Members-Only Breakfast with Santa at the Maritime Aquarium
Saturday, December 6, 8 a.m. – 10 a.m.
This event is for members only

Pancake Breakfast with Santa at the Boys & Girls Club of Greenwich
Saturday, December 6, 8 a.m. – 11 a.m.

Breakfast with Santa and Stew’s Costumed Characters at Stew Leonard’s Norwalk
Saturday, December 13 & Sunday, December 14, 8:30 a.m. & 10 a.m.

Claus, Crafts, and Carols at 314 Beer Garden
Saturday, December 13, 1 p.m. – 3 p.m.

Breakfast with Santa at The IC
Sunday, December 14, 9 a.m. – 11 a.m.

Tony’s Brunch with Santa
Sunday, December 14, 10 a.m. – 3 p.m.
Click here for a reservation!

Breakfast with Santa at Wright Tech High School
Saturday, December 20, 9 a.m. – 11:30 a.m.

Brunch with Santa
Saturday, December 20, noon – 3 p.m. Sign of the Whale
Call (475) 250-2662 for a 
reservation

Restaurants for Christmas Eve Brunch/Dinner

Prime Stamford
Farmhouse at the Crossroads
Table 104
Divina
The Ridges
The Wheel at the Village

Open Christmas Day

Lenny’s Steakhouse
Lyla’s Restaurant
Terra Gaucha Brazilian Steakhouse
Taj Indian Cuisine
Blackstones Steakhouse
Çka Ka Qëllu
Tony’s at the J House
L’Escale
MŌLÌ

Additional Holiday Info:

The Stamford Moms Holiday Event Guide
Ways to Give Back
Where to Cut Your Christmas Tree This Year
Where to Get Your Christmas Tree in Stamford
The 2025 Stamford & Greenwich Holiday Catering Guide
Tips for the Essex Steam Train North Pole Express

Join The Stamford Moms Network Community

Stay up-to-date with what is happening in-and-around the Stamford community with local events, community highlights, and exclusive deals.