Dedham Restaurants
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Il Massimo - Legacy Place
Price: Expensive•Italian•4.7(2,922)From Joseph and Esther DeQuattro of Pane Vino and Il Massimo of Federal Hill comes the much anticipated Il Massimo at Legacy Place. Il Massimo brings the quintessential Italian trattoria to Dedham, Massachusetts.
At IL Massimo we are proud to offer a seasonal Italian menu inspired by the regional cuisines of Italy. Signature dishes include Spaghettoni alla Carbonara with guanciale and a farm fresh egg, Point Judith Calamari en Padella, and the Pesce al Guazzetto with fresh local fish and little neck clams.Tavern in the Square - Dedham
Price: Moderate•American•4.6(618)We are located at 985 Providence Highway in Dedham with a private parking lot, large bar, multiple tv's and a private dining room for your next party. If you are looking for a place to celebrate a special occasion, take the family out for a great dinner, or get together with a group of friends to watch a game then we are the spot for you. We offer a variety of options on our menu as well as local beers and handcrafted cocktails.
Liberty & MAIN
Price: Expensive•American•4.4(936)Located in Legacy Place in Dedham, MA, Liberty & MAIN is a classic American bistro featuring an interactive bar and seasonal outdoor patio. Locally owned and operated by restaurant veteran and former CEO & President of The Smith & Wollensky Group, Michael Feighery, our menu features only the freshest, locally sourced ingredients. Dishes represent both American bistro classics and new favorites crafted and presented in an imaginative and thoughtful manner by restaurant Executive Chef, Doug Brown. Our signature Grilled Peanut Butter & Bacon is a dish you do not want to miss!Orchid 7 Fusion Bar & Grill
Price: Expensive•Caribbean•4.3(45)Orchid 7 Fusion Bar & Grill is a full-service restaurant based in Massachusetts. We proudly offer a wide selection of brunch, lunch, dinner, and desserts with a unique fusion and fun twist. Our extensive main menu and drink menu are crafted with meticulous care.
At Orchid 7, our talented Chef Team has a world-class repertoire and has boldly reimagined Fusion Caribbean cuisine. Drawing inspiration from the vibrant colors, flavors, and aromas of the Caribbean, Africa, Europe, and Latin America, our kitchen seamlessly brings together culinary influences from diverse regions. The chefs' creative vision is daring, unexplored, and forward-reaching.
Outdoor dining in Greater Boston
See what locals rave about in Dedham
- PPaulVIPGreater Boston •136 reviews4.0Dined 3 days agoAnother nice visit to Il Massimo. Very busy and very energetic (meaning loud). Service was good - our waitress was friendly, professional, and did her best to service the table, but because she had, in my opinion, too many table assignments, service was very slow. It took way too long to get our orders taken. She was great, but over-assigned. Food was great. Large servings - decent quality. Wine list was good - average pricing is about 2-1/2 times retail in most cases, which is acceptable. Overall, we will continue to return to Il Massimo.More infoIl Massimo - Legacy PlacePrice: Expensive• Italian• Dedham•4.7
- CChrisGreater Boston •1 review5.0Dined 4 days agoService was excellent as expected. Crabcake w lobster was delicious as were the sirloins - especially mine with shrimp and what seemed like a lobstery sauce. Be sure to note if it’s a special occasion (was our anniversary) - the staff really treats you well (wishing us happy anniv, placing a card on the table, complimentary dessert, and took our photo for a keepsake!)More infoThe Capital Grille - DedhamPrice: Very Expensive• Steakhouse• Dedham•4.8
- AAnneVIPGreater Boston •7 reviews5.0Dined 5 days agoFirst shift for our server. She was very professional and pleasant. Food was delicious as usualMore infoTavern in the Square - DedhamPrice: Moderate• American• Dedham•4.6
- PPeterVIPGreater Boston •4 reviews5.0Dined 7 days agoOverall very good but cost was too high. Cost was on par with Capital zgrille, but ambience and value was belowMore infoLegal C Bar - DedhamPrice: Expensive• Seafood• Dedham•4.3
- PPeterGreater Boston •3 reviews5.0Dined on Jun 3, 2025Great service. Olivia was fantastic! The food was great especially the Boa Buns and the desserts. Great Chocolate Martinis. Great ambiance. Will definitely go back.More infoLiberty & MAINPrice: Expensive• American• Dedham•4.4
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Discover Dedham
The suburb of Boston, Dedham, and the surrounding area provides a plethora of unique restaurants with signature dishes. High-end restaurants serving 8-course meals exist among bistros serving burgers. Seek out an establishment offering authentic clam chowder, or Boston chowder, a thick soup made with clams, cream, potatoes, butter, and onions. Of course, you can’t leave Dedham without trying a lobster roll, piles of lobster meat with mayonnaise served on a bun, but why not try some more unique lobster dishes as well? Lobster spaghetti, lobster-stuffed dumplings, or lobster stew can be found at various establishments. If you’re looking for some comfort food, taste some of the Dedham area’s authentic Boston baked beans.
Frequently asked questions
The best reviewed restaurant in Dedham is The Capital Grille - Dedham
The best vegan restaurants in Dedham are Il Massimo - Legacy Place, The Capital Grille - Dedham and Legal C Bar - Dedham
The best vegetarian restaurants in Dedham are Il Massimo - Legacy Place, Tavern in the Square - Dedham and Liberty & MAIN
The restaurants with the best service in Dedham are Il Massimo - Legacy Place, The Capital Grille - Dedham and Tavern in the Square - Dedham
The restaurants with the best ambiance in Dedham are The Capital Grille - Dedham, Il Massimo - Legacy Place and Liberty & MAIN
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