Top 10 Best Day Trips from Massachusetts

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Massachusetts's location in the heart of the northeast New England region makes it a good base for day trips to some of America's most cherished historic sites ... read more...

  1. Portland is a city located at the confluence of the Willamette and Columbia rivers in the state of Oregon. It is only a two-hour drive, or Amtrak's Downeaster schedule from Boston gives you seven hours to savor a seafood lunch or early dinner at a waterfront restaurant and an afternoon of browsing in the boutiques and galleries in Portland's historic downtown.

    Edgecomb Potters create pottery inspired by the sea and mountains; Lisa-Marie's Made in Maine carries jewelry, art, and specialty foods; and Maine Craft Portland in the historic Mechanics Hall showcases local talent. At Sea Bags Factory Store on Custom House Wharf, you can watch as skilled artisans recycle sea-worn sails into smart totes and bags. Or spend your time in this port side city visiting the excellent Portland Museum of Art or in the extraordinary rooms of the Victoria Mansion, one of America's most important 19th-century historic homes. Portland has a West Coast climate that is warm in the summer and rainy but mild in the winter. The weather is perfect for growing roses and for over a century Portland has been known as the Rose City for its numerous rose gardens - especially famous as the International Rose Experimental Garden.

    Willamette and Columbia, Oregon, United States
    Distance from Delaware: 500 miles
    Travel time: 8 hours
    TripAdvisor Review: 33,239 reviews

  2. In the early 20th century, New York's super-wealthy decamped for the summer to Newport, where they vied with one another to see who could build the biggest and most extravagant mansion. Many of those palatial summer residences are open today, either preserved or restored to their glittering glory. Look for echoes of the Grand Trianon and other European royal palaces, which several used as inspiration for their own excesses.

    Marble House has an opulent salon, lined with pounds of gold leaf, and a fanciful Chinese Tea House. Less ostentatious and more livable, but no less grand, is Doris Duke's Rough Point, where her art collection is displayed. Follow Bellevue Avenue to see the public faces, then at least a part of the famous Cliff Walk to see these mansions from the shoreside. You can tour two of the most opulent of these - The Breakers and The Elms - on the Boston to Newport Small-Group Day Trip with Breakers & Elms Mansion, traveling by air-conditioned coach with a guide who will add perspectives about Newport's history, culture, and architecture. There is time to stroll along Newport's waterfront for shopping before returning to Boston.

    Location: Newport County, Rhode Island, United States


    Distance from Delaware: 84 miles
    Travel time
    : 1 hour 32 minutes
    TripAdvisor Review
    : 12,8343 reviews
  3. Top 3


    Once a more important port than Boston, and the center of America's prosperous China Trade, Salem retains much of its 18th- and 19th-century architecture, with entire neighborhoods of imposing homes that were built for successful merchants and sea captains. Retained, too, are memories of its grimmer early history as the scene of the Salem Witch Trials. Several of the finest homes are open to tour, furnished with generations of fine antiques and with decorative arts brought from the Far East.

    The 1727 Crowninshield-Bentley House and the 1684 John Ward House are part of the outstanding Peabody Essex Museum, whose art and historical collections highlight maritime subjects, the China Trade, and Asian arts. Among its treasures is a fully furnished original 18th-century house from China's Huizhou region. The Salem Maritime National Historic Site includes the docks, a replica sailing ship, the Customs House, warehouses, exhibits, the historic Pickering Wharf, and two historic homes. The fastest and most convenient way to get to Salem from Massachusetts is on the Boston to Salem High Speed Ferry, which departs Boston's Long Wharf and arrives in Salem within a few steps of the House of the Seven Gables.

    Location: Essex County, Commonwealth of Massachusetts, United States


    Distance from Delaware: 35 miles

    Travel time: 40 minutes

    TripAdvisor Review: 3,016 reviews
  4. The Stellwagen Bank, an underwater plateau in the Atlantic off the Massachusetts coast, has one of the world's most biologically productive ocean environments, which makes it one of the best places to study and spot whales. The sanctuary lies within Massachusetts Bay, 25 miles east of Boston, 5 miles east of Gloucester, and 5 miles north of Provincetown, Massachusetts. Sightings are so frequent that some whale-watch cruises come with a guarantee of a free trip if no whales appear. Most commonly observed are female humpback whales that return to these waters, which are especially rich in food, to teach their young to hunt.

    Whale watching has become a major industry and recreational activity with the primary focus on humpback whales due to their reliable presence and dramatic behaviors. In addition to the humpback whales, there is a good chance of seeing other whale species, Atlantic white-sided dolphins, harbor porpoises, seals, and other marine life. Researchers from the Whale Center of New England accompany the three-hour Boston Whale Watching Cruise to explain the whales' habits and habitat and discuss their conservation status and scientific tracking methods. Schedules vary, but most companies offer trips from the beginning of May until the end of October, although several may start earlier or end later in the season.

    Location: Massachusetts Bay, Massachusetts, United States
    Distance from Delaware:
    90 miles

    Travel time: 50 minutes

    Fee: $40 per person

    TripAdvisor Review: 1,577 reviews
  5. Old Sturbridge Village is a living museum located in Sturbridge, Massachusetts which recreates life in rural New England during the 1790s through 1830s. It is the largest living museum in New England, covering more than 200 acres. The Old Village includes 59 antique buildings, three water-powered mills, and a working farm. The museum is popular among tourists and for educational field trips.

    More than 40 historic buildings form the open-air museum at Old Sturbridge Village - gracious homes of the well-to-do, rustic farmhouses, a parsonage, village store, tavern, and workshops where tinsmiths, blacksmiths, printers, potters, and coopers demonstrate their crafts. Along with touring Old Sturbridge Village, where you'll find costumed interpreters cooking in fireplaces, tending their gardens, spinning, sewing, and doing needlework, you can watch logs become boards in a water-driven sawmill and take part in activities. A working farm grows period vegetables and herbs, and the farmyard is alive with animals that have been back-bred for authenticity. The large herb garden is especially interesting as it grows many of the plants that were used in everyday life at the time, for flavoring, medicines, cosmetics, and dying wool.

    Location: 1 Old Sturbridge Village Rd, Sturbridge, MA 01566, United States
    Distance from Delaware:
    342 miles
    Travel time:
    5 hours
    Tel: 1 800-733-1830
    : 9:30 AM - 17:30 PM
    $14 per person
    TripAdvisor Review:
    1,428 reviews
  6. Strawbery Banke is unique among outdoor history museums in presenting a complete neighborhood’s evolution over 300 years, with most of the historic houses on their original foundations. These structures link visitors to the people who lived on the Portsmouth waterfront from 1695 to 1954. Costumed roleplayers and traditional craftspeople recreate the lives, concerns, and challenges of families in the community, basing their interpretations on diaries, letters, historical records, archaeology, and collected artifacts.

    The first settlers in 1623 called their new home Strawbery Banke, and today, the ten-acre Strawbery Banke Museum preserves houses from four centuries of the old Puddle Dock neighborhood beside the harbor. Some are preserved to show their construction and the process of restoration, others are furnished to represent a period in their history, and others are "inhabited" by costumed interpreters who tell their stories through demonstrations and daily activities. Together the houses show life at various periods and of the different ethnic groups who lived here. You can see a neighborhood market from the World War II era, watch as authentic Gundalow boats are built, stroll in period gardens, and tour the elegant home of a former governor.

    14 Hancock St, Portsmouth, NH 03801, United States
    Distance from Delaware:
    400 miles
    Travel time:
    7 hours
    1 603-433-1100
    10:00 AM - 17:00 PM
    $17.5 to $19.5 per person
    TripAdvisor Review:
    1,333 reviews
  7. The Wrentham Village Premium Outlets is an open-air outlet power center owned by Simon Property Group. It is located off I-495 and Route 1A in Wrentham, Massachusetts. The facility opened in 1997 and was expanded in 1998, 1999, and 2000. With 616,000 sq ft and 170 retailers, it has been credited as the reason for the downfall of the nearby, smaller Worcester Common Outlets, which closed in 2006, as well as the Cape Cod Factory Outlet Mall, which closed in 2011. In September 2018, the Simon Property Group began a multiphase and multimillion-dollar renovation of the center.

    Ardent shoppers will find it hard to resist the lure of 170 outlet stores in one place. That's what you'll find at Wrentham Village Premium Outlets, about 45 minutes south of Boston. Nearly all the stores are outlets of major name brands, including high-end brands such as Salvatore Ferragamo, Brooks Brothers, and Burberry. In the stores, shoppers find deeply discounted prices on brand-name clothing, housewares, shoes, electronics, jewelry, accessories, decor, and gifts. Look for Banana Republic, Calvin Klein, Aéropostale, American Eagle Outfitters, HugoBoss, Bloomingdale's, Le Creuset, Saks OFF Fifth, and more. Shoppers who arrive by tour bus usually get complimentary VIP coupon books for even greater discounts.

    Location: Wrentham, Massachusetts, United States


    Distance from Delaware: 300 miles

    Travel time: 6 hours

    Tel: 1 508-384-0600

    Hour: 01:00 AM - 21:00 PM

    Fee: Free

    TripAdvisor Review: 733 reviews
  8. Martha's Vineyard is one of the best day trips from Massachusetts. From Falmouth, on the south coast of Cape Cod, the Island Queen Ferry sails across Vineyard Sound to Oak Bluffs, on the island of Martha's Vineyard. You won't need a car to explore this beautiful island: just hop on and off the handy transit bus to see lighthouses, Aquinnah Cliffs, historic Edgartown's art galleries, and the gingerbread cottages at Oak Bluffs.

    You probably won't be able to see all six of The Vineyard's towns in a day, but you can visit the two largest, and perhaps even take the cute little ferry to Chappaquiddick Island. Along with touring the interior of one of the Victorian cottages in Oak Bluffs, take a ride on the Flying Horses Carousel. For a glimpse of life through the island's 400-year history, visit the 1672 Vincent House in the former whaling port of Edgartown. A Day Trip to Martha's Vineyard from Boston takes you by coach to the town of Falmouth, where you'll board the ferry to the island. Here, you'll have six hours to explore on your own, and plenty of time to hop the transit bus and see the highlights, using the island discount card that's included with the tour.

    Location: Cape Cod, Massachusetts, United States


    Distance from Delaware: 107 miles

    Travel time: 2 hours 50 minutes

    TripAdvisor Review: 653 reviews
  9. Thanks to Interstate-93, you can drive from the Boston area directly into the heart of New Hampshire's rugged White Mountains. Because much of New Hampshire's forest land - protected by the White Mountain National Forest, is hardwoods, the foliage is spectacular, with the bright reds and oranges of maple, yellow birch leaves, and all shades in between.

    Several mountains, including Mt. Washington, the highest peak in the northeast, have tramways, gondolas, and even a train to the summits for even more sweeping views. These mountaintop rides are the region's prime tourist attractions, as is the drive over the Kancamagus Pass on the Kancamagus Highway. This winding route reaches the highest elevation of any public road in the northeast. To see the highlights, you can travel by air-conditioned coach on the Boston to New Hampshire Fall Foliage White Mountains Day Trip, with pickup at your hotel. The full-day tour travels over the Kancamagus Pass, with photo stops, and stops in North Conway, where you'll have time to enjoy shopping and lunch along the attractive main street.

    Location: New Hampshire, United States


    Distance from Delaware: 500 miles
    Travel time
    : 8 hours
    : 1,917 m

    Tel: 1 800-346-3687

    TripAdvisor Review: 236 reviews
  10. Newburyport is a coastal city in Essex County, Massachusetts, United States, 35 miles northeast of Boston. The population was 18,289 at the 2020 census. A historic seaport with a vibrant tourism industry, Newburyport includes part of Plum Island. The mooring, winter storage, and maintenance of recreational boats, motor, and sail, still contribute a large part of the city's income. A Coast Guard station oversees boating activity, especially in the sometimes dangerous tidal currents of the Merrimack River.

    About 35 miles north of Boston, Newburyport's history as a prosperous maritime port shows in its beautiful Federal homes. The city is part of Massachusetts' North Shore; Newburyport was laid out on the elevated south bank of the Merrimack River between the river and Newbury marshes. The shipyards, now boatyards, extended along the bank at the edge of the river. Colonial residences extend up the bank from Merrimac Street to High Street running parallel to it near the top of the ridge. Many feature widow's walks, and structures on the roof where the residents could watch for the return of sailing vessels. You could spend a day just admiring the architecture of these beautifully preserved buildings.

    Location: Essex County, Massachusetts, United States


    Distance from Delaware: 52 miles

    Travel time: 1 hour

    TripAdvisor Review: 105 reviews

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