11 Unforgettable Fall Getaways From Boston
Boston, home to a variety of excellent venues and locales such as Fenway Park and Beacon Hill, is not necessarily recognized as a great place to avoid the hustle and bustle of city life. Luckily, there are several small towns, resorts, and even state parks located less than a three-hour drive from downtown Boston. Small towns like Marblehead, Massachusetts, located less than an hour away, and North Conway, New Hampshire, no more than a two-and-a-half-hour drive from the city, quickly provide the ability to enjoy the pleasures of small-town America, at least for the day. From autumn-inspired festivals to the stunning fall foliage colors seen all across New England, these eleven small towns are truly unforgettable.
Marblehead, Massachusetts
The coastal town of Marblehead, less than 45 minutes away from Boston’s northern border, is a perfect oasis for those who wish to get away, at least for the day. Marblehead provides several natural attractions that encourage visitors to return every fall, including the Marblehead Neck Wildlife Sanctuary and Crowninshield Island, formerly named Brown’s Island, which is located on Massachusetts Bay and can be reached by boat or even sometimes by wading out at low tide. There are also several fall festivals held annually in Marblehead, like the Fall Fair, which takes place every October and features activities for kids, including pumpkin picking and lawn games, as well as a well-maintained garden for the adults to enjoy.
Mystic, Connecticut
Less than two hours southwest of downtown Boston, the quaint town of Mystic is known for a plethora of natural amenities that showcase the wonders of autumn, as well as the beauty of fall foliage in Connecticut. Olde Mistick Village, famous for portraying how time used to be, caters to several events that present that once-a-year experience, including the Garlic Festival in September and the Apple Festival in October. Along with offering an authentic taste of the autumn season through apple pie bake-offs, syrup samplings, and pumpkin carvings, these festivals also offer face painting, various food vendors, and balloon artistry. Plus, just outside of town, visitors can enjoy the Denison Pequotsepos Nature Center, which has a variety of animals, from hawks and falcons to foxes and deer.
Portsmouth, New Hampshire
Portsmouth, just over an hour’s drive away from Boston and known best for being the oldest settlement in New Hampshire, has a variety of natural amenities that showcase the beauty of autumn each year. There are several great hiking trails that can be enjoyed by even amateur travelers in Portsmouth. Little Harbor Loop Trail, beginning at Sagamore Creek, and Prescott Park Loop, overlooking Piscatagua River, are just two of several breathtaking trails that provide that taste of the stunning beauty of nature during the autumn season. Downtown Portsmouth also hosts many events that showcase the fall foliage and the culmination of the summer season, including the Pumpkin Smash, taking place at the local farmers’ market in October.
Westerly, Rhode Island
Less than a two-hour drive southwest of Boston, the quaint and cozy town of Westerly, Rhode Island, is a natural haven for those who wish to escape the city, at least for the weekend. Filled with a plethora of natural attributes that draw in tourists throughout summer and autumn, like the Napatree Point Conservative Center and Misquamicut Beach, the town of Westerly also attracts people through a variety of festivals and events directly geared toward the autumn season and the prismatic colors of fall foliage. The Misquamicut Fall Festival takes place every year in the middle of September at Misquamicut Beach, offering amusement rides, live music from various artists, and even a variety of food and craft vendors, selling everything from caramel apples to belt buckles.
Stockbridge, Massachusetts
Two hours straight west of the city of Boston, the town of Stockbridge has a variety of activities that complement the beauty of fall foliage in Massachusetts. Naumkeag offers much more than the breathtaking vistas that can be experienced within its gardens, including the Naumkeag Pumpkin Show, which has showings three or four times every week from the end of September until just before Halloween. Known best for the Norman Rockwell Museum, Stockbridge also has several trails that challenge physical endurance while still captivating the eyes with the colors of New England in September. Laura’s Tower Trail and the Ice Glen Trail are two of the more difficult trails available.
Kennebunkport, Maine
The picturesque town of Kennebunkport is famous for many historic and cultural venues and attributes like Saint Ann’s Church, President Bush’s summer compound, and the Seashore Trolley Museum. Yet, this Maine coastal town offers a variety of natural experiences. There are several activities that can be enjoyed during the autumn season that cannot always be enjoyed during the heat of summer or the cold of winter. Only just under two hours away from Boston, visitors can hike several trails, including Parson’s Way and the Goose Rocks Beach Walk, both offering scenic views of the coast and the majestic Atlantic Ocean. Kennebunkport is also home to a variety of community-lead fall festivals, like the Fall Family Festival, which takes place at “The Lodge on the Cove” and features a pumpkin scavenger hunt, potato sack races, and pumpkin painting contests.
Rockport, Massachusetts
Home of the Halibut Point State Park, which features excellent hiking and fishing opportunities, Rockport is one of the best (and closest) getaway locales in the area. Only an hour from the city are Front Beach, Gully Point Cove, and several scenic walking trails and paths, including Hellcat Dunes Loop and the Dogtown Woods Circular. The Hellcat Dunes Loop is just over a mile long and is wheelchair accessible, while the Dogtown Woods Circular is seven miles in length, a bit more difficult, and loops around Peter’s Pulpit. There are also a variety of autumn-oriented festivals in and around Rockport, including Rockport Harvestfest, which takes place every October and showcases the wonders of fall and the bounty of the harvest.
Provincetown, Massachusetts
Perhaps one of the most popular coastal towns in close proximity to Boston, as it is only a two-hour drive from the city, picturesque Provincetown has a plethora of natural summer attractions, like Race Point Beach and Herring Cove Beach. Yet, since Provincetown is actually situated at the tip of Cape Cod, the wonders of the Atlantic Coast can be experienced through many attributes during the fall season as well. Provincetown hosts several great autumn festivals annually, including celebrating "Women's Week," honoring women everywhere with dance parties, dune tours, and even a community dinner, and "Halloween in Provincetown," showcasing everything from pumpkin-related activities to costume competitions.
Jackson, New Hampshire
The town of Jackson, situated in the heart of the White Mountains and located less than three hours north of Boston, is a town that welcomes nature with open arms. Home of Jackson Falls, Glen Ellis Falls, and Honeymoon Bridge, one of several covered bridges in New England, this town of a thousand permanent residents is not only considered to be the gateway to the White Mountains, but it is also home to several natural facets and fall attractions, including Pinkham Notch, Black Mountain, and Crawford Notch. Several fall festivals are also held in and near the town of Jackson, including the “All Things Pumpkin Festival,” which occurs every October and features activities such as horse-drawn carriage rides, pumpkin carving contests, and even a pumpkin pie-eating challenge.
Ogunquit, Maine
Less than an hour and a half from Boston and slightly less of a road trip than traveling up to North Conway, the tiny town of Ogunquit, Maine, is a little over an hour’s drive from the city and has around four miles of beaches, the Leavitt Theater, and Marginal Way, which begins near downtown Ogunquit, meanders between the Atlantic and the mainland and ends less than two miles later at Perkins Cove. There are also a variety of other attributes that cater to nature and the wonders of autumn in New England in Ogunquit, including several stunning hiking trails. The Hilton-Winn Preserve Loop, the Ogunquit River Trail, and Nahum’s Way all offer some breathtaking vistas of the fall foliage turning from greens and yellows to reds and oranges.
North Conway, New Hampshire
The pastoral town of North Conway is a true haven for experiencing some of the most vibrant fall foliage in all of New England. Just under three hours away from Boston, North Conway is home to the Conway Scenic Railroad, which offers a plethora of stunning scenic vistas while traveling through Mt. Washington Valley and parts of the White Mountains. North Conway, known as one of the premier getaway locations in New Hampshire, is also in close proximity to Echo Lake State Park, which offers a variety of great nature trails, and the Kancamagus Scenic Byway, a 35-mile-long trip through the White Mountain National Forest on a two-lane road, following the twists and turns of the Swift River.
Embrace the Best of Autumn Near Boston
Are you looking for an autumn-inspired festival, such as the Fall Fair in Marblehead or the Naumkeag Pumpkin Show in Stockbridge? Are you craving a taste of the fall foliage, watching the stunning colors of the forest changing from green to red, orange, and yellow? Whether it is an event inspired by the town, a bonfire out back of a comfy resort, or an all-natural attraction like Front Beach in Rockport, these eleven locales allow us to experience the autumn season in the best way possible.
