There's nothing quite like Fall in Boston. As the air turns brisk and the leaves start to change, the Boston area transforms into an autumnal paradise that charms even the most experienced traveler. But, the Fall fun isn't just confined to Boston. From Concord to Cape Cod, you'll discover unforgettable experiences beyond just Boston this Fall.

North of Boston


With Halloween around the corner, it's the perfect time to visit Salem. Check out the popular Salem Witch Museum and learn how the town earned its aptly named moniker Witch City. Art and cultural aficionados will want to spend time at the Peabody Essex Museum to peruse its collections highlighting three centuries of maritime history and Asian trade. If you're visiting during October, plan to attend Salem's annual Haunted Happenings, which are considered by many as the largest celebration of Halloween on earth.

Gloucester & Rockport

Escape the hustle and bustle of Boston for a day at the harbor town of Gloucester,  America’s oldest seaport renowned for commercial fishing and whale watching.  Stay the weekend at the Beauport Hotel, a boutique waterfront setting on Cape Ann. Nearby is the charming seaside town of Rockport, home to one of the oldest art colonies in America. Known for its quirky galleries on Main Road and Bearskin Neck, Rockport has inspired artists since Winslow Homer. 

New Hampshire & Maine

There's no better way to experience an iconic New England Fall than with a short trip from Boston to New Hampshire or Maine! Enjoy lush scenery and colorful views during an overnight stay in New Hampshire's White Mountains. Or opt for a day trip aboard a comfortable bus, complete with spectacular picture-taking moments, on Gray Line’s Fall Foliage sightseeing tour. Deal-seeking shoppers can enjoy outdoor splendor with a day trip to the Kittery Outlets, about an hour from Boston in Kittery, Maine. Twenty minutes farther north, consider a retreat at Cliff House Maine, a destination that stretches across 70 oceanfront acres atop the majestic Bald Head Cliff.


Explore more destinations north of Boston here.


Concord & Lexington, and more

For a sublime day of recreation consider hiking or biking the Minuteman Trail, a ten-mile stretch that passes through towns with rich literary and Revolutionary War Era history. Hop on the Liberty Ride trolley and learn the history of the Battles of Lexington and Concord, narrated by tour guides in colonial costumes. The 90-minute tour will take you to notable landmarks, such as the Concord Museum and Emerson House. Stay the night at the Inn at Hastings Park and treat yourself to a phenomenal dining experience on-site at Town Meeting restaurant. Spend the day leaf-peeping on Nashua River Rail Trail in Groton and rest up at the Groton Inn. Continue a little farther west to Wachusett Mountain for big events and festivals such as AppleFest and the Fall Food Truck Festival.

Explore more destinations West of Boston here.



If you’re heading south of Boston, consider a stop in Quincy. There are a variety of things to do in this picturesque city by the bay. Stroll around Marina Bay and catch a glimpse of the beautiful Boston skyline from afar or walk Wollaston Beach to savor the last traces of summer. Drive inland towards Adams National Historical Park, the homes of two past Presidents, John Adams and John Quincy Adams. Perfect your game at Granite Links, a semi-private golf club located in the scenic Quarry Hills.


Just a few miles farther south is Plymouth, the site of the first pilgrim settlement in the country. Find out how Native Americans and Pilgrims lived at Plimoth Plantation in a detailed walking tour through a re-created 17th-century village. Seaport lovers will also appreciate New Bedford, a city lined with historic squares, cobblestone streets and intriguing attractions such as the New Bedford Whaling Museum, the Palmer’s Island Lighthouse and Battleship Cove.


Sitting on the tip of Cape Cod is Provincetown, easily accessible by ferries from Boston’s Bay State Cruise Company or Boston Harbor Cruises. A popular destination for the LGBTQ community, the town boasts beautiful beaches, top-rated restaurants, art galleries and charming shops. Why not extend your stay on the Cape and catch up on some quality sleep at the grand Inn at Cape Cod?

Take advantage of “off-season” rates and visit the picturesque islands of Nantucket or Martha’s Vineyard by ferry services from Hy-Line Cruises or Steamship Authority. For a truly elegant experience, make reservations at the White Elephant, a charming island landmark since the 1920s.


Explore more destinations South of Boston here.