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, 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. If you're visiting in October, plan to attend Salem's annual Haunted Happenings. Widely regarded as one of the largest Halloween celebrations on Earth, from Halloween balls to ghost tours, and their Grand Parade, this event brings a plethora of events to enjoy daily. Book a highly sought after day trip to Salem in October with FTI Coach to experience Salem’s Haunted Happenings with ease. Tickets stop selling mid-September so be sure to plan ahead. Arrive by boat, as the early settlers did, with Boston Harbor City Cruises and learn the true story behind the peculiar happenings of the 1692 Salem Witch Trials with their guided Legacy of Witches tour. If you’re looking for a shorter trip, consider a half a day trip with Don Quijote Tours, exploring both Salem and Marblehead, a seaside town with beautiful views just 15 minutes from Salem. Art and culture aficionados will want to spend time at the Peabody Essex Museum to peruse its collections highlighting three centuries of maritime history and Asian trade.

Gloucester & Rockport

Escape the hustle and bustle of Boston for a day in the harbor town of Gloucester, America’s oldest seaport renowned for commercial fishing and whale watching. Stop by the Hammonds Castle Museum and enjoy the beauty of the castle grounds and rocky Atlantic coast. Book a Don Quijote Tour and spend the day exploring the North Shore, including Marblehead, Salem, Gloucester, and Rockport. Stay the weekend at the Beauport Hotel, a boutique waterfront setting on Cape Ann. Hop aboard the luxurious dinner ship, the Beauport Princess, and spend some time cruising the Historic Gloucester Harbor. 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. While there, consider taking a scenic road trip on the Kancamagus Highway, a winding road lined with trees that guide you through the White Mountain National Forest, providing captivating views of the Fall foliage. Visit the AppleCrest Farm/Orchard in Hampton Falls on your way up for some pumpkin and apple picking. If visiting during October, book the Fall Foliage at Castle in the Clouds Day Trip with FTI Coach to experience the best of Fall foliage in New Hampshire.

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. For a convenient way to discover many of the charming towns of Maine, reserve a day trip in early October to the Southern Maine Coast with New England Trips.

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. Consider booking a Fall Foliage and History day trip from Boston with New England Trips or a half a day trip with Don Quijote Tours to experience the beauty of these historic towns in the Fall with ease. 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. Take some time to explore the scenic trails and stunning skyline views of the Blue Hills Reservation. Afterward, enjoy a comfortable stay at the Quincy Marriott, conveniently located just a five-minute drive away, and end your evening at the Hull and Mason Restaurant and Bar located within the Marriott.


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 Patuxet Museums in a detailed walking tour through a re-created 17th-century village. If you get a chance, take a leaf peeping, casual stroll through the charming Brewster Gardens, located in Brook, Plymouth. The garden is filled with lush plants, statues and rolling lawns with a picturesque trail running alongside the stream. Reserve a Plymouth Day Trip with New England Trips and embark on a journey through time as you explore numerous historical sites in the charming South Shore cities and towns, including Quincy, Weymouth, and beyond, until finally reaching “America’s Hometown” Plymouth MA. Opt for a shorter adventure and book a half-day trip with Don Quijote Tours to explore Plymouth Rock, the Plantation, and more. 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. 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. Book a Martha’s Vineyard Day Trip with New England Trips, featuring a three-hour narrated tour of the island. For a truly elegant experience, make reservations at the White Elephant, a charming island landmark since the 1920s. If visiting during late October, be sure to attend Martha’s Vineyard Food and Wine Festival in honor of the islands talented culinary artists.

Explore more destinations South of Boston here.