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The Top 30 Memorial Day to Labor Day Weekend New England Travel Ideas

Swan Boats of Boston, Massachusetts

Swan Boats of Boston in Boston, Mass.
by Eric Hurwitz. Updated 12/02/16.

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  No "Freebird" or "Stairway to Heaven" number one finishes here, or the drone of counting down 500 songs over the holiday weekend -- just the top 30 best New England
 
Memorial Day to Labor Day weekend New England summer travel destinations, counting down to number one! Some destinations like Hyannis, MA., Watch Hill, RI, Old Orchard Beach, Maine and Newport, RI, have a live wire, seaside feel, while places like Old Lyme, Conn., Jackson, NH, Northeast Harbor, Maine, and Deerfield, MA, offer rest and relaxation in more tranquil, quiet settings. Whatever the case, here are our top 30 Memorial Day to Labor Day vacation destinations -- places that just feel right to visit at the beginning of summer:

30. Bristol, RI -- In simple terms, Bristol is a great waterfront town, one of the most appealing in New England. Surrounded by Mount Hope Bay to the east and Narragansett Bay to the south and west, Bristol features breathtaking water views and an "all-American" ideal downtown featuring wonderful local shops, inns and restaurants. Nearby Colt State Park, affords amazing views of the Narragansett Bay and a terrific place to walk or bike (the great East Bay Bike Path). Bristol is close to famous Newport, RI, and wonderfully revitalized Providence, R.I., making it a perfect foundation for your Rhode Island vacation. Book a room in Bristol

29. Scituate, MA -- This South Shore Boston, MA, suburb offers seaside Cape Cod charm without going over the "bridge" and the traffic that goes with it. Scituate offers small beaches, a beautiful lighthouse at Scituate Light, a wonderful downtown with locally-owned stores, and terrific seafood restaurants like the Mill Wharf (with a splendid view of Scituate Harbor). Book a room in Scituate

28. Jackson, NH -- Hiking, biking, canoeing, kayaking, waterfalls, mountain streams, covered bridges make Jackson a terrific natural summer place. Close proximity to all Mt. Washington region activities, and plenty of charming inns and bed and breakfasts to stay result in Jackson being a clear choice for those looking for a quiet quintessential New England community in a wonderfully relaxing mountainside region. Book a room in Jackson

27. Old Lyme, CT -- This quiet coastal Connecticut town has little going for it except beautiful, old New England homes, access to the coast and relaxing walks along non-commercial Main Street. That's enough for us. The Bee and Thistle and Old Lyme in are renowned local, historic inns. Book a room in Old Lyme

26. Deerfield, MA -- Deerfield boasts about a mile of historic Main Street homes and the prep school presence of famous Deerfield Academy. It's close to other interesting western Massachusetts communities and college towns like Amherst and Northampton. Like Old Lyme, this is an ideal place if you like peace and quiet. If you're looking for lots of things to do, however, go elsewhere, although the mammoth Yankee Candle Factory a few miles from the Main Street provides the ultimate gift shopping experience in a building that is more like a shopping mall. Book a room in Deerfield

25. Hampton Beach, NH -- A fantastic Atlantic Coast beach, arcade games, weekly fireworks displays, 80 free summer concerts, restaurants and shops highlight this bustling southern New Hampshire resort town. Not always clean and with too many clothing challenged "show-offs," Hampton Beach might not be for everyone, but there is something for everyone. You can find your own quiet spot, or go with the loud crowds. Hampton Beach has been a long time favorite New England vacation destination; millions of visitors through the years can't be wrong. For many, a Memorial Day excursion to Hampton Beach is a way of life and a validation that summer has begun. Book a room at Ashworth by the Sea in Hampton Beach

24. North Conway, NH -- It isn't what is used to be with all the outlet stores coming into town, but North Conway still remains one of the most beautiful settings in New England, courtesy of an amazing Main Street view of Mt. Washington (highest elevation in New England at 6,288 ft.). There's still plenty of small town charm and close proximity to the significant amount of natural and theme park attractions in the White Mountain region. There's also no shortage of restaurants with around 100 choices, ranging from pizza to new American. Book a room in North Conway

23. Plymouth, MA -- Plimoth Plantation, Plimoth Rock and other pilgrim-related attractions combine with some nice ocean beaches and seafood restaurants to make Plymouth a recommended southern New England destination. "America's hometown" has witnessed a tremendous turnaround in its downtown section -- now filled a pleasant mix of  locally-owned shops, galleries, boutiques, and restaurants. Book a room in Plymouth

22. Litchfield, CT -- With almost a collegiate feel -- with no college -- Litchfield is a favorite "New Yorkers" destinations with its tree-lined streets, fine but limited restaurant scene and a quiet, historic aura blessed with a pretty town common. Litchfield, from many profiles, is the epitome of true New England. Book a room in Litchfield

21. Hanover, NH -- The ultimate college town, thanks to the esteemed Dartmouth College. A community vibrancy and many restaurants, walking destinations and arts and entertainment opportunities make Hanover a nice place to visit. It's near the Vermont border and not too far from the southwest regions of the White Mountains. Book a room in Hanover

20. Ipswich, MA -- This small North Shore Massachusetts town features Crane's Beach, one of the great ocean beaches on the Atlantic Coast. Famous Rockport and Gloucester are nearby. Book a room in Ipswich

19. Hyannis, MA -- Commercial, loud and full of youths and families, Hyannis may not be your relaxing Cape Cod getaway but its quite fun with its plethora of beaches, ice cream, miniature golf, candle and cranberry-fueled gift shops and nightlife. Just a few minutes away on Old Route 6A, you have the chance to unwind in classic Cape Cod communities like Yarmouthport, Barnstable and Sandwich. Book a room in Hyannis

18. Rye, NH -- Traditional motels,seafood stands and public ocean beaches mix with spectacular ocean homes on the impressive New Hampshire seacoast. Rye is near other great New England vacation destinations like Portsmouth, NH, Hampton Beach, NH, and York, Maine. Book a room in Rye

17. Watch Hill, RI (Westerly) -- Watch Hill Beach, in Westerly, delivers the seaside family beach setting that prospective New England travelers envision. Safe, scenic and seemingly always sunny, the beach is surrounded by a charming village of shops (candy, books, beachwear, arts and crafts, boutiques, etc), seafood restaurants, a magnificent carousel and enough ice cream places to bring out the best in summer. The neighborhoods boast fine old sea captain's homes. Book a room in Westerly

16. Stockbridge, MA -- Norman Rockwell called Stockbridge "the best of America, the best of New England," and it's easy to see why. Stockbridge is picture-perfect with its wide Main street, tree-lined neighborhoods, great flower displays, proud homes, fresh air and community hospitality. This is the perfect Berkshire Mountain town, perfect for relaxation and a stroll down one of the Northeast's most pleasant Main Streets.  Book a room in Stockbridge

15. Freeport, Maine -- The ultimate outlet store town, with L.L. Bean leading the way. Over 170 outlet stores should be enough to keep the most dedicated, obsessed shopper busy, but we remind you please not to forget the nearby spectacular Maine coastline. Freeport is not too far from Portland, a great waterfront city, and the well-maintained historic communities of Bath, Brunswick as well as picturesque Boothbay Harbor. Book a room in Freeport

14. Old Orchard Beach, Maine -- A large ocean beach, boardwalk with shops and restaurants, an amusement area with rides and games and endless souvenir shops make Old Orchard a crowded, fun-filled Maine vacation destination for the family. It can be, as one friend said, "a drain on society" with somewhat of a crude, bonehead crowd, but it's generally safe... and so much fun! Book a room in Old Orchard Beach

13. Centerville, MA -- The relaxing Craigsville Beach and the amazing Four Seas Ice cream Stand (canatalope ice cream, anyone?) is enough to start anyone's Cape Cod Memorial Day Weekend. Centerville is near the commercial mecca of downtown Hyannis, but shares little of its commercialism. It is, in fact, a peaceful Cape Cod destination that you would come to expect from a previous generation. Book a room near Centerville

12. Kennebunkport, Maine -- Former president George Bush, Sr., lives here; he couldn't have picked a better location. Kennebunkport's downtown might just be the best for a small Maine town -- full of great little shops, historic and majestic inns and bed and breakfasts, and terrific seafood restaurants. It looks like Maine here (you'd be surprised how many Maine towns have lost that special look due to over-commercialism). From popular ocean beaches downtown to the quiet seaside of Goose Rocks Beach on the outskirts, Kennebunkport is a near-perfect coastal Maine vacation destination. Book a room in Kennebunkport

11. Burlington, VT -- Blessed with amazing views of Lake Champlain, Burlington is a big, fun college town (University of Vermont and several others) with enough arts and entertainment, a four block pedestrian shopping area, and enough mountain and lake scenery to keep visitors coming back and residents permanently residing in what is called a "mini-San Francisco" by some. With a restaurant scene worthy of bigger cities and scenic places to walk reminiscent of a peaceful small vacation town, Burlington brings together the best of urban and small town New England.  Book a hotel in Burlington, Vermont

10 Newport, RI -- A high concentration of spectacular mansions and an even higher concentration of shops and restaurants make Newport a famous, appealing ocean vacation spot. It's bit hectic downtown, but the outskirts near Fort Adams State Park are just as peaceful as ever -- a true representation of a relaxing New England coastal experience. Book a room in Newport

9. Portsmouth, NH -- Forget about what author Bill Bryson says about Portsmouth being unforgettable. This small southern New Hampshire seacoast city has so much going on that it makes you wonder why you should bother with some of the bigger cities. Mixing the traditional with the chic, Portsmouth has a nice downtown with old-time stores, trendy shops, an amazing concentration of old sea captain's homes, Prescott Park by the harbor and historic, outdoor museum Strawberry Banke.This is New Hampshire's oldest seacoast neighborhood where one can experience Portsmouth life from the late 1600s to the 1950s. Add a spirited community feel, some terrific seafood restaurants (the Oar House) and a safe feel, and you'll see why Portsmouth has become an "A" list New England travel destination. Book a room in Portsmouth

8. Lexington-Concord, MA -- Home of the Revolutionary War, this period of history can be seen in the town commons, old, historic homes, museums and guided tours. We prefer Concord as it's a little less suburban, has some beautiful countryside and offers the great Walden Pond for swimming and hiking.  Book a room in Concord

7. Stowe, VT -- Often thought of as a great skiing destination, Stowe, Vt., is also a wonderful summer place to vacation. Attractively tucked away between Mt. Mansfield and other spectacular mountains and hills, Stowe has a high concentration of dining, lodging, shopping and recreational opportunities. At times, Stowe looks overly commercial outside the 200-year-old downtown village with its myriad shops, but let's face it -- the mix of gift and art shops, restaurants (like the great casual Shed), and motels, inns and bed and breakfasts are of such high quality that they serve a valuable purpose. There's no obnoxious, hokiness here. Downtown, the site of a general store, a church rising above the trees and the local coffee shop bring out the best in small-town New England living, although some say it is more reminiscent of a mountainside European Village. Close by in Waterbury is the Ben and Jerry's Ice Cream headquarters, where the tour is fun and free samples are available. Cold Hollow Cider Mill is another highlight, also in Waterbury. They make cider the old-fashioned way with a rack and cloth press built in the 1920s. Cider is not the only attraction at this legendary attraction as a bakery (including delicious homemade donuts), Green Mountain Coffee, Vermont-made wines and a toy store are just a few of the thousands of items found at this delightful roadside building. On the north side, a ride through the rugged, scenic notch into Jeffersonville, will have your car twisting and turning into high elevations that provide some unforgettable forested, rocky scenery. This is just the tip of the iceberg in Stowe; it is a place to do lots of things, or just relax and do nothing within a peaceful environment. That is the beauty of Stowe.  Book a room in Stowe

6. Rockport, MA -- Rockport has done a great job of retaining its New England flavor by refusing to become too over commercial. That leaves you with a quaint New England town, flavored by the renowned artist colony at Bearskin Neck, some fine ocean beaches and seafood restaurants that represent the best of New England. Rockport is part of the vacation oriented North Shore featuring nearby Salem, Gloucester, Marblehead, and Essex. Rockport can stand on its own as a vacation destination, or as part of a total package. Book a room in Rockport

5. Lincoln-Woodstock region, NH -- The beautiful White Mountains provide the scenery and tourist attractions like the Flume Gorge, Clark's Trading Post (with live trained bears), the Loon Mountain gondola, the Mt. Washington cog railway, Cannon Mountain Aerial Tramway and Hobo Railway make this region a clear preferred family destination. Famous and beloved lodging like the Indian Head, Woodward's, Jack O'Lantern and Loon Mountain Resort provide the perfect foundation to this traditional favorite travel destination. Book a room in Lincoln

4. Boston, MA -- An amazing array of the old and the new, Boston is one of America's great cities. The historic Freedom Trail leads the way to old Italian neighborhoods (North End), upscale European-like shopping and residential districts (Newbury Street), the Swan Boats of Boston boat rides in the Boston Public Garden (pictured at top of page), the restaurants and stores at wonderfully restored Old Faneuil Hall, Fenway Park (the Boston Red Sox), upscale Beacon Hill with its great brownstones, and about a million other attractions so vast that even a lifelong Bostonian will never get to full experience. Book a room in Boston

3. Block Island, RI -- Block Island resembles Martha's Vineyard, but without the overwhelming crowds of expense. Block Island may have a busy-- and necessary downtown filled with shops, lodging and dining but once you're past this section, it's all unspoiled terrains with green land and incredible ocean views from the clay cliffs. There's plenty of beach space for families. The Nature Conservancy has designated as "one of the 12 last great places in the Western Hemisphere." It's the perfect place to bike or use a motor scooter to view the wonderful natural settings. Book a room at Block Island

2. Northeast Harbor, Maine -- A peaceful haven from some of the more commercial hustle and bustle of Acadia National Park, Northeast Harbor is a true vacation getaway. Situated on a beautiful Maine harbor, Northeast Harbor also has a quaint little downtown with a grocery store, a few restaurants and clothing and antique stores. It feels tucked away in the middle of nowhere, but is just minutes from all of Acadia's major scenic attractions. It is our preferred choice when seeking a natural, peaceful vacation in Acadia National Park. Book a room in Northeast Harbor

1. York Beach, Maine -- If the Beach Boys were East Coast born, their hit single "Fun, Fun, Fun" would have been dedicated to York Beach, Maine. Two fine family-oriented ocean beaches (Short and Long Sands), a zoo and amusement park (York Kingdom) a dizzying array of souvenir shops, a salt water taffy store (Goldenroad's), great seafood restaurants, the famous Nubble Lighthouse and Dunn's Ice Cream stand (with its blueberry ice cream) make York Beach a must when visiting New England. It has the best vacation feel of any New England destination, balancing relaxation with enough fun things to do. This is the ultimate place to walk the beach, eat lobster, and admire the rocky Maine coast. What more could you ask for in New England?  Book a room in York Beach


Short Sands Beach, York Beach, Maine
Short Sands Beach, York Beach, Maine

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