Holiday Kingdom Trail
Expiration: Jan 3rd 2026
This year, we’re excited to introduce the NEW Holiday Kingdom Trail, a fun way to explore Downtown all season long! Check in at to earn points, unlock rewards, and discover hidden gems—from festive drinks and treats to unique shops and winter attractions. Turn every holiday outing into an adventure as you collect points and redeem them for prizes across the Holiday Kingdom.
Included Venues
See locations on an interactive map.
Artisan Bistro stands as an unparalleled bistro experience in Boston, where our chefs reimagine classic dishes with elevated flair. Our inviting bar provides the perfect setting for an aperitif, completing your exceptional private dining in Boston.
Avery Bar, located off the lobby in The Ritz-Carlton, Boston, is evocative of a luxurious living room designed to welcome hotel guests. Unwind over craft cocktails and shareable plates at this exquisite bar in downtown Boston.
Back Deck offers professional backyard grilling in a laid-back city setting seven days a week. Friends and family meet for charcoal-grilled favorites inspired by the food served at casual cookouts along with porch-perfect cocktails, beer and wine.
What's Included
- Holiday Gift Card Bonus – Get 20% More!
Welcome to Bakey Babka! Our mission is to bring our love of this gooey delicious baked good to our own community in Boston. Our pastries are served fresh from the oven, from sunrise to sunset! Babka is a sweet braided bread which originated in the Jewish communities of Europe.
Experience American roadside classics elevated with high-level technique and obsessive sourcing. Our signature 3.5 oz burgers are smashed to order and served with tallow onions, ripe tomatoes, and Grin Sauce on herb-toasted potato buns. Simple, sweet, and seriously satisfying.
Stop by for soft serve with a special gingerbread cookie.
The Brattle Book Shop, founded in the Cornhill section of Boston in 1825, has been in the hands of the Gloss Family since 1949. Over the years George and his son Kenneth built this shop into one of the largest antiquarian book shops in the country.
Housed in a three-story building in the heart of Downtown Boston, The Brattle Book Shop carries an impressive stock of over 250,000 books, maps, prints, postcards and ephemeral items in all subjects. In addition to its general used and out-of-print stock, The Brattle Book Shop also maintains an inventory of first editions, collectibles and fine leather bindings in its rare book room.
Enjoy juicy, fall-off-the-bone chicken in three crave-worthy styles — zesty lemon pepper, bold spicy, and golden crispy tenders. Raised free-range and cooked with care, Chika brings flavor you can feel good about, paired with vibrant sides and sweet finishes like our signature Twinkie Tres Leches.
Stop by for a special Mexican chocolate cookie with marshmallow!
Welcome to Day Shift, where modern café culture meets the heart of downtown Boston. Located inside the Winthrop Center at The Lineup food hall, we offer more than just great coffee — we’re your morning jumpstart, mid-day fuel, and afternoon recharge. From house-roasted espresso to savory sandwiches and handmade pastries, Day Shift has something delicious for everyone.
Enjoy the Hot Cocoa Bar! Complete with all your favorite add-ons like marshmallows, candy canes, whipped cream, and more sweet holiday fixings!
Whether you're looking for a large dining room table to share the warmth of company with a few plates of appetizers, or just need a cozy nook to find shelter from downtown Boston's cold winter winds, Democracy Brewing invites you to spend your holiday season with us! Grab a seat at the bar and order a pint of our seasonal draft beers or try a flight of four. Pair your beverage with one of our rotating holiday food specials, and if beer isn't your thing, we also offer seltzer-based cocktails!
Estella Restaurant is a culinary gem in the heart of downtown Boston. Our space celebrates unity, culture, and the story of our founder’s mother, Estella, whose legacy is woven into the soul of the restaurant. From intimate dining to lively entertainment, our multi level layout gives every guest a unique experience. You can learn more about us here:
French Quarter, a slice of New Orleans, is located in Downtown Boston at 545 Washington Street, between the Opera House and Paramount. The restaurant brings vibrant, bold, unique New Orleans style food and cocktails to the neighborhood, in a visually stunning space filled with the sounds, smells, and welcome feel of Louisiana.
What's Included
- Holiday Gift Card Bonus – Get 20% More!
Savor authentic Neapolitan pizzas crafted from Chef Fraser's signature dough with perfect leopard-spotted crusts, ready in just 90 seconds. Don't miss our signature pie with golden yellow tomato vodka sauce and citrus-marinated shrimp, plus an array of spuntini (small plates) and Italian-inspired sandwiches.
Stop by for festive cannolis!
Follow the HolidayTrails to High Street Place, where festive flavors and cozy cocktails bring the holiday spirit to life. With over 20 unique restaurants and bars, it’s the perfect spot to eat, drink, and be merry. Gather with friends or take a break from holiday shopping in our warm, welcoming food hall. Celebrate the season in the heart of Downtown Boston — deliciously
Enjoy vibrant Greek flavors with healthy, seasonal bowls and pitas inspired by Eastern Mediterranean food stalls. Fresh ingredients and accessible Greek cuisine perfect for Boston's busy lifestyle, offering both nutritious and flavorful options.
Stop by for Greek Christmas cookies(Kourabiedes)!
Tucked away above Governor’s Alley, on a historic 18th-century patio, MAST’ specializes in Old World-style pizza, using its special wood-fired oven. Awarded Top Restaurant in the World Gambero Rosso & Boston’s Only VPN Certified Pizza & Neapolitan Cuisine.
Check out 1 of 12 giant, illuminated, animal-themed Nutcrackers in Downtown! These 16 foot tall, illuminated figures surprise and delight, both day and night.
Check out 1 of 12 giant, illuminated, animal-themed Nutcrackers in Downtown! These 16 foot tall, illuminated figures surprise and delight, both day and night.
Check out 1 of 12 giant, illuminated, animal-themed Nutcrackers in Downtown! These 16 foot tall, illuminated figures surprise and delight, both day and night.
Check out 1 of 12 giant, illuminated, animal-themed Nutcrackers in Downtown! These 16 foot tall, illuminated figures surprise and delight, both day and night.
Check out 1 of 12 giant, illuminated, animal-themed Nutcrackers in Downtown! These 16 foot tall, illuminated figures surprise and delight, both day and night.
Check out 1 of 12 giant, illuminated, animal-themed Nutcrackers in Downtown! These 16 foot tall, illuminated figures surprise and delight, both day and night.
Check out 1 of 12 giant, illuminated, animal-themed Nutcrackers in Downtown! These 16 foot tall, illuminated figures surprise and delight, both day and night.
Check out 1 of 12 giant, illuminated, animal-themed Nutcrackers in Downtown! These 16 foot tall, illuminated figures surprise and delight, both day and night.
Check out 1 of 12 giant, illuminated, animal-themed Nutcrackers in Downtown! These 16 foot tall, illuminated figures surprise and delight, both day and night.
Check out 1 of 12 giant, illuminated, animal-themed Nutcrackers in Downtown! These 16 foot tall, illuminated figures surprise and delight, both day and night.
Check out 1 of 12 giant, illuminated, animal-themed Nutcrackers in Downtown! These 16 foot tall, illuminated figures surprise and delight, both day and night.
Check out 1 of 12 giant, illuminated, animal-themed Nutcrackers in Downtown! These 16 foot tall, illuminated figures surprise and delight, both day and night.
Old Corner Christmas Store is a year-round Christmas shop with over 5,000 ornaments. Visitors can explore everything from classic favorites to one-of-a-kind treasures.
The concept for SIP Cafe was built on Europeanstyle cafés found in public spaces in such places as Italy, France, Germany, and Denmark. The enduring quality of these café’s is how they spill-out along street edges, into parks and public spaces. Come visit the SIP experience.
The Merchant, which opened in March 2014, is an American brasserie serving lunch, dinner, late-nite, oyster bar, 36 drafts, craft cocktails and two private dining rooms. Located in the former London Harness space–a leather shop that counted Benjamin Franklin among its early customers–The Merchant offers more than 60 beers, plus wine (including three on tap) and cocktails.
Experience the magic of the season at The Ritz-Carlton, Boston, where timeless elegance meets festive charm. Step inside our beautifully adorned lobby and take in the sparkling décor inspired by the spirit of the holidays. Join us for a meal at Artisan Bistro or a festive cocktail at Avery Bar, and celebrate the warmth and wonder of winter in downtown Boston.
What's Included
- Free Dessert With Purchase Of Entree