Enjoy the Magic of Fall in Boston, Massachusetts

• Explore the Freedom Trail: This 2.5-mile red-brick path takes you through 16 historical sites. The fall foliage adds a beautiful backdrop to your walk.

• Boston Commons and Public Garden: Enjoy the vibrant autumn colors in these iconic parks. Don’t miss the swan boats at the Public Garden!

• Sample Seasonal Foods: Head to Nathaniel Hall, Boston’s famed Food Market for pumpkin spice treats, apple cider donuts and hearty New England clam chowder.

• Walk Along the Charles River Esplanade: Enjoy a leisurely stroll or bike ride along the river, taking in the stunning views and fall colors.

• Take a harbor cruise: For a spin on the classic Boston harbor cruises that are offered, take a pedal-boat cruise with Cycle Boat Boston. You can pedal to propel the boat or relax in the lounge.

• Newbury Street: A historic avenue known for its high-end boutiques, art galleries, cozy cafes and charming brownstones. It’s the perfect way to enjoy a fall afternoon in Boston.

• Cannoli and Cocktails: There’s no better way to experience Boston’s North End than with a Cocktails and Cannoli Tour.

Day Trips

If you have extra time, consider a day trip to nearby destinations like Salem for its Halloween festivities or Concord for its historical significance.

• Contessa, a glass-enclosed rooftop restaurant atop the Newbury Hotel serving up Northern Italian. Currently one of Boston’s hottest restaurants.

• The Long Bar & Terrace: Another rooftop spot not to be missed is the Long Bar at the Raffles Hotel, the first one to open in the United States. Enjoy all-day dining, high tea and craft cocktails.

• Grana: Set in a former federal bank, Grana’s soaring ceilings and luxe décor set the scene for a fabulous meal. Brunch is the true highlight here.

• Union Oyster House: As one of the oldest restaurants in the US, this historic spot offers classic New England cuisine, including clam chowder and fresh seafood, perfect for the cooler weather.

• The Capital Grille: Known for its dry-aged steaks and extensive wine list, this upscale steakhouse provides a cozy atmosphere ideal for enjoying hearty meals during fall.

• Tatte Bakery and Café: Tzurit Or, the founder behind Tatte, started the bakery 16 years ago, selling their baked goods at Copley Square’s Farmers Market. Now you can enjoy hearty salads, sandwiches and of course, baked goods, at the brick-and-mortar location in the Boston Seaport.

• Legal Sea Foods: Yes, it’s a chain, but honestly it’s popular for good reason. The seafood restaurant consistently serves great clam chowder and steamed lobsters. Even the location in the airport is fantastic.

• Oleana: Located in Cambridge, Oleana offers Mediterranean-inspired dishes with locally sourced ingredients. The outdoor patio is beautiful in the fall, surrounded by colorful foliage.

• Assaggio: For Italian food that is truly comfort food, head to this cozy, bi-level restaurant in the heart of Boston's North End neighborhood.

• Saltie Girl: Famous for its seafood and fresh catches, Saltie Girl offers a unique twist on New England classics. Their lobster rolls are a must-try!