New England

Out & About | Best New England Fall Events for 2018

Enjoy Octoberfest, the sight of 5,000 lighted pumpkins, and more, at these top picks for New England fall events.

By Yankee Magazine

Aug 09 2018


It’s been joked that Head of the Charles competitors who fail to make the sharp turn at the Weeks Footbridge, foreground, will end up rowing right through Harvard Square.

Photo Credit : Carlos Ridruejo/courtesy of HOCR


It’s been joked that Head of the Charles competitors who fail to make the sharp turn at the Weeks Footbridge, foreground, will end up rowing right through Harvard Square.
Photo Credit : Carlos Ridruejo/courtesy of HOCR



Returning for its sixth year with fresh wind in its sails, this nautical party on New London’s waterfront has grown from three to five days of free, family-oriented fun. Among the highlights: tours of Navy and Coast Guard ships, a chowder cook-off, a schooner race, and a “Swingin’ on the Pier” dance party. 860-447-2519;



Head to Sunday River to see couples put an athletic spin on the vow “To have and to hold” as each man totes his female partner over a 278-foot-long race course featuring, among other obstacles, a water hazard nicknamed “the widow-maker.” The top pair wins beer, cash, and a chance to compete in the world championship in Finland—the country that first gave us this unusual spousal sport.



Only the Boston Marathon draws more sports spectators to the city than this, the world’s largest rowing regatta. Founded in 1965, it now attracts 300,000-plus people to the banks of the Charles River to watch both novices and champions navigate the famously tortuous three-mile course (and dodge seven bridges along the way). 617-868-6200;

New Hampshire


The good folks of Auburn offer a big dose of small-town fun, all wrapped up in a tidy one-day package. Come for the apple pie contest, square dancing, kids’ games, Civil War encampment, and homemade crafts and goodies from local makers, but most of all for the spectacle of 3,000-plus rubber duckies bobbing over the Griffin Dam in the 26th annual Duck Race.

Rhode Island


The only thing more magical than walking through the seasonal display of 5,000 lighted pumpkins at Providence’s Roger Williams Park Zoo? Flying over it on the zoo’s Soaring Eagle Zip Ride, which for a modest extra fee will carry you up to 115 feet high on a side-by-side bench seat (which for our money is far comfier than a broomstick). 401-785-3510;



German culture comes to a head at West Dover’s Mount Snow Resort with this beer-centric weekend, which offers not only fine brews but also a stein-holding contest, a keg toss, and a “Gulp and Gallop” beer run. There’s plenty to amuse tots and teetotalers, too, from oompah music and yodeling to face painting, games, and hearty German fare. 800-245-7669;


AUG. 31–SEP. 3: SOUTH WOODSTOCK, Woodstock Fair. Animals and exhibitions, entertainment on multiple stages, amusement rides, contests and family fun, plus more than 100 food vendors offering everything from treats to rib-sticking meals. 860-928-3246;

SEP. 7–9: NORWALK,Oyster Festival. Oysters may be the headliners, but the festivities go far beyond shucking and slurping. Veterans Park will rock with day-to-evening musical performances, international foods, kids’ activities, a lumberjack show, and a juried arts and crafts show featuring more than 100 exhibitors. 203-838-9444;

SEP. 28–30, OCT. 5–7: SOUTHINGTON,Apple Harvest Festival. Join in the family fun, including a parade, toe-tapping musical performances, an arts and crafts show, carnival rides, and fireworks. And come hungry: There will be apple crisp, apple pie, apple fritters, apple slushies, and fresh raw apples aplenty. 860-276-8461;

SEP. 29: WETHERSFIELD, Old Wethersfield Arts and Crafts Fair. Peruse the wares presented by 100-plus artisans and crafters—clothing, furniture, seasonal decorations, jewelry, and more—while soaking up the fall weather, live music, and tasty food at scenic Cove Park. 860-529-7656;

SEP. 30: WESTPORT, Chowdafest.With participants from every New England state and beyond, Chowdafest has become one of the largest culinary competitions in the Northeast. Vote for your favorites at Sherwood Island State Park as chefs and restaurants compete in the categories of classic New England clam chowder, traditional chowder, creative chowder, soups and bisques, and—new in the lineup—vegetarian chowder. 203-216-8452;

OCT. 6–7: BETHLEHEM,Garlic & Harvest Festival. Spice up your life with a trip to the Bethlehem Fairgrounds, where garlic lovers will find goodies showcasing their favorite allium, from garlic dips and spreads to deep-fried garlic, garlic sausage, and even garlic ice cream. Also on tap are cooking demos, crafts, rides and games, and live entertainment. 203-266-7810;

OCT. 7: SCOTLAND,Highland Games Festival. Immerse yourself in the sights, sounds, and flavors of Scotland as the Edward Waldo Homestead hosts a day filled with entertainment and education. There’s something happening everywhere you turn: live folk music, dancing, piping and drumming contests, sheepdog demonstrations, and, of course, the fabled Highland athletic competition. Cabers away!

OCT. 26: HARTFORD,Hallowed History Lantern Tour. Established in 1864, Cedar Hill Cemetery welcomes nighttime visitors to its graceful grounds just once each year. Starring in this evening of spooky fun are actors portraying some of the dearly departed (many with dark tales to tell). Space is limited, so reserve your spot well in advance. 860-956-3311;


AUG. 31–SEP. 1: CAMDEN,Camden Windjammer Festival. Midcoast Maine’s famous cruising fleet gathers to say good-bye to summer with a last blast of maritime excitement. Visitors can take in a parade of sail, fireworks show, lobster crate race, build-a-boat contest, nautical dog competition, fish relay, and

AUG. 31–SEP. 9: BOOTHBAY HARBOR,Boothbay Region Harbor Fest. This lively mix of music, food, and activities includes a 5K run and a half-marathon, a fashion show inspired by the sea, a restaurant crawl, wellness events, art sales, a vintage market, and live musical performances at venues all around the harbor. 207-671-7676;

SEP. 5–9: BAR HARBOR,Acadia Night Sky Festival. Come see the Milky Way shining bright in the largest expanse of naturally dark sky east of the Mississippi. This annual community celebration is full of options for soaking up the celestial sights, from cruises on Frenchman Bay to guided night hikes. Take advantage of the chance to learn from and with scientists, park rangers, photographers, artists, and fellow stargazers. 207-801-2566;

SEP. 7–9: EASTPORT,Eastport Pirate Festival. Hark back to days of yore, when pirates were no strangers to the Maine coast. Come in costume—if you’d like to blend in—and enjoy wacky activities including bed races and pirate reenactments, along with live music, lobster boat races, and kids’ games. 207-853-4343;

SEP. 8: STATEWIDE, Open Lighthouse Day. This popular event offers the public the rare opportunity to explore more than two dozen of Maine’s historic lights. The lineup changes annually, so check out the website for updated info on this year’s locations. 207-594-4174;

SEP. 21–23: UNITY,Common Ground Country Fair. Hosted by the Maine Organic Farmers and Gardeners Association, this annual get-together pays tribute to the rural and agricultural traditions of Maine with animal exhibits, cooking demos, blacksmithing, farm and fiber marketplaces, a social and political action area, tasty food, and kids’ programming. 207-568-4141;

SEP. 30–OCT. 7: FRYEBURG,Fryeburg Fair. This venerable fair (c. 1851) fills its eight-day run with livestock shows, races and competitions, and an array of garden and craft exhibits, plus midway rides and entertainment across five stages, all at the Fryeburg Fairgrounds. Don’t miss the Woodsmen’s Field Day, which draws lumberjacks and lumberjills from across the U.S. to test their mettle. 207-935-3268;

OCT. 5–8: DAMARISCOTTA,Pumpkinfest & Regatta. A giant-pumpkin contest, pumpkin catapult, pumpkin derby, pumpkin drop, pumpkin pie eating contest—perhaps you’re detecting a theme? Don’t miss the great pumpkin boat regatta finale. 207-677-3087;


SEP. 14–30: WEST SPRINGFIELD,The Big E. When it comes to big fairs in New England, it’s impossible to top this, the sixth largest agricultural fair in the entire country. Its mind-boggling array of food (barbecue brisket sundae, anyone?) keeps fairgoers fueled up for fun that ranges from agricultural competitions to midway rides, top-notch musical acts, and those amazing butter sculptures. 413-737-2443;

SEP. 22–23: DEERFIELD,Old Deerfield Fall Craft Fair. The historic village of Old Deerfield provides a picturesque setting for browsers as they peruse jewelry, furniture, and more on the grounds of one of New England’s oldest museums, Memorial Hall Museum. 413-774-7476;

SEPT. 28–OCT. 8: TOPSFIELD,Topsfield Fair. The country’s oldest continuously operating fair—which hits its 200-year anniversary this fall—just keeps getting better. Enjoy headline entertainment and shows, 4-H competitions, midway rides, games, tempting treats, and more. 978-887-5000;

OCT. 4: SALEM,Haunted Happenings Grand Parade. Though Salem’s Haunted Happenings festival runs throughout the month of October, the big costume parade is the town’s time-honored kickoff for the Halloween season. This year’s theme is “The Magic of Hocus Pocus,” so expect to see witches, wizards, and magicians galore. 978-744-0004;

OCT. 6–7: WAREHAM,Cranberry Harvest Celebration. Hosted by the A.D. Makepeace Company, the world’s largest cranberry grower and a founder of the Ocean Spray growers’ co-op, this event invites you to come see cranberries being harvested and learn how the fruit is incorporated into cooking and crafts, all while enjoying live music, a farmers’ market, paddleboat rides, and the varied offerings of area craft and food vendors.

OCT. 11–14: BOSTON,Taste of WGBH Food and WineFestival. Held at the WGBH studios in Boston’s Brighton neighborhood, this extravaganza of flavors brings together New England’s top chefs, producers, wineries, and breweries, creating a sampling bonanza. Further spicing things up are live music performances and celebrity chef demonstrations that in past years have included such PBS favorites such as Mary Ann Esposito and the Brass Sisters.

OCT. 13: BOSTON,Boston Book Festival. Celebrating the “power of words to stimulate, agitate, unite, delight, and inspire,” this free Copley Square festival marks its 10th year with a schedule chock-full of author readings and panels, plus a street fair, in the heart of downtown Boston. 857-259-6999;

OCT. 13–14: WELLFLEET,OysterFest.Give a nod to the town’s famous bivalves and fishing traditions with hometown fun and flavor. Lures include local cuisine (heavy on the seafood), arts and crafts, a marine-themed spelling bee, walking tours, live music, a 5K road race, and the must-see “oyster shuck-off” competition. 508-349-3499;

OCT. 17–21: EDGARTOWN,Martha’s Vineyard Food & Wine Festival. Join Yankee in toasting the island’s rich tradition of farming and fishing with local culinary talent, and the farmers, fishermen, oyster producers, and artisans they work with. 508-939-0199;

New Hampshire

SEP. 7–9: HAMPTON BEACH,Hampton Beach Seafood Festival. Live music and a fireworks show punctuate the seafood-eating frenzy as festivalgoers sample delicacies from 60-odd local restaurants. Also on tap: chef demos, arts and crafts booths, a sidewalk sale, and a lobster-roll eating competition. 603-926-8718;

SEP. 13–16: PLYMOUTH,White Mountain Storytelling Festival. Feel the power of the spoken word at Plymouth State University as accomplished tale-spinners hold forth. Don’t miss the Friday-night slate of hair-raising ghost stories.

SEP. 15: ENFIELD,Harvest Festival.Among the old-school diversions on offer at the Enfield Shaker Museum: Take a wagon ride; make cider, churn butter, and crank your own ice cream; and dip handmade candles and learn other traditional crafts. 603-632-4346;

SEP. 21–23: LINCOLN,New Hampshire Highland Games. Don your tartan and step lively as Loon Mountain hosts more than 30 pipe bands and competitions in dance, fiddle, and harp, plus athletic contests, a clan village, sheepdog trials, and special ticketed events like a whiskey tasting and a harp concert. 603-229-1975;

SEP. 27–30: DEERFIELD,Deerfield Fair. Dating back to 1876, the Deerfield Fair bills itself as “New England’s oldest family fair.” It’s also one of the biggest fairs in New Hampshire, with livestock pulls and exhibitions, a demolition derby, sheepshearing, midway rides, live entertainment, and all your favorite fair food. 603-463-7421;

OCT. 6: DOVER,Apple Harvest Day. More than 400 vendors, artisans, and organizations make for a busy scene downtown during this family-focused event, which comprises a craft fair, five stages of live entertainment, a 5K, an apple pie contest, and dozens of kids’ activities. 603-742-2218;

OCT. 6–8: MONADNOCK REGION,Art Tour. Enhance a foliage drive through this picturesque region by picking up a map and following the “Art Tour” signs leading to the homes and studios of artists in towns including Dublin, Harrisville, and Peterborough. Have a visit, ask questions, and view a variety of fine artwork. Studios are open from 10 a.m. to 5 p.m. daily.

OCT. 12–13: LACONIA,New Hampshire Pumpkin Festival. In addition to the obvious draw (20,000 carved pumpkins clustered around downtown, including those lined up on a 34-foot tower), offerings include fair foods and rides, live musical performances, and don’t-miss events such as a pumpkin pancake breakfast, a pumpkin cook-off, and a zombie walk.

OCT. 26–27: PORTSMOUTH,Ghosts on the Banke. Long-dead sea captains, 17th-century shopkeepers, and wayward privateers haunt the streets of Strawbery Banke, Portsmouth’s oldest neighborhood, as you trick-or-treat by jack-o’-lantern light. 603-433-1100;

Rhode Island

AUG. 31–SEP. 3: CHARLESTOWN,Rhythm & Roots Festival. With more than 40 musical acts on the roster—including the Taj Mahal Trio, Asleep at the Wheel, and CJ Chenier & the Red Hot Louisiana Band—this Ninigret Park festival promises a rocking Labor Day weekend.

SEP. 8: PAWTUCKET,Chinese Dragon Boat Races & Taiwan Day Festival. Watch the colorful dragon boats—crewed by both professionals and amateurs—as they race along the Seekonk River, and then join in the fun on land (think: cultural performances, an arts and crafts display, and a dumpling eating contest). 401-724-2200;

SEP. 21–23: BLOCK ISLAND,Taste of Block Island. More than just a culinary event, this weekend aims to give the full flavor of Block Island. Over 50 local businesses join together to host a variety of gallery openings, wine and beer tastings, and tours, while offering discounts and specials at a number of shops, hotels, and restaurants, too. 401-466-2474;

SEP. 22: LINCOLN,Great Road Day. Nine historical sites along the 17th-century highway Great Road (today’s Route 123) welcome the public with free admission today, including “the house that love built,” Hearthside; the architecturally rare “stone-ender” Arnold House; and the c. 1812 Moffeet Mill. 617-227-3956;

SEP. 29–30: MIDDLETOWN,Harvest Fair. If you’ve never been to the natural treasure that is the 325-acre Norman Bird Sanctuary, this long-running old-timey fair is a great excuse to visit. Among the highlights are barrel train rides, pony rides, a mud pit, midway games, and a crafters’ tent—with plenty of food and music, too. 401-846-2577;

OCT. 6–8: NORTH SCITUATE,Scituate Art Festival. What began as a way to pay for restoring the handsome 1830s Congregational church on the village green has evolved into a major event that draws 200-plus exhibitors from across North America. Proceeds go toward town nonprofits—as well as the maintenance effort to keep that old church sparkling.

oct. 13–14: BRISTOL,Coggeshall Farm Harvest Fair. A traditional autumn event with 18th-century flavor comes to the bucolic grounds of Coggeshall Farm Museum. Perfect your aim in the seed spitting contest, take sides in a tug-of-war, see artisans at work, visit with some farm animals, and generally unplug from the 21st century. 401-253-9062;

OCT. 13–14: NEWPORT,Bowen’s Wharf Seafood Festival. Savor the bounty of the sea as presented by area restaurants and fishermen’s associations. There’s lobster, chowder, stuffed quahogs, clam cakes, shrimp, scallops, raw oysters, and clams, as well as dishes tailored for kids and/or landlubbers. Local-favorite bands keep the beat while you eat. 401-849-2243;


AUG. 24–SEP. 2: ESSEX JUNCTION,Champlain Valley Fair. Expect loads of classic fair fun with 4-H events, horse pulls, cooking contests, and the judging of everything from home-brewed beer to Christmas trees. Headlining the music lineup on Aug. 31: ’80s hitmakers Rick Springfield, Eddie Money, Greg Kihn, and Tommy Tutone. 802-878-5545;

SEP. 2: RANDOLPH,New World Festival. A spirited tribute to the vitality of small-town Vermont and the Celtic/French-Canadian heritage of northern New England, this full-day event offers continuous music, storytelling, and dance at various venues around town. 802-728-6464;

SEP. 7–9: BURLINGTON,South End Art Hop. Visit the city’s original arts district and discover thousands of works of art as well as outdoor sculpture, performance art, live demos and workshops, kids’ activities, and a fashion show. 802-859-9222;

SEP. 13–16: TUNBRIDGE,Tunbridge World’s Fair. Head to the fairgrounds to explore family-farm traditions from the past, view antique machinery and implements, and tour an authentic one-room schoolhouse. Also on the lineup: pig races, harness racing, livestock and gardening competitions, fair foods, and an old-fashioned carnival. 800-889-5555;

SEP. 29: BURKE,Fall Foliage Festival.Autumn in a small town doesn’t get any better than this. Come enjoy horse-drawn wagon rides, a rubber duck race, a parade, a petting zoo, live music, a tag sale, and more. 802-626-4124;

SEP. 29–30: TUNBRIDGE,Vermont Sheep and Wool Festival.Small farms and natural fibers are the focus as more than 70 vendors offer fleece and yarn, fiber crafts, and other homespun wares. Check out the classes and workshops, herding and shearing demos, and local music—and don’t forget the maple creemees! 802-685-3267;

OCT. 5–7: STOWE,Foliage Arts Festival. More than 150 juried artisans will bring their creations to Topnotch Field for the area’s biggest autumn arts festival, complete with food, wine, beer, and entertainment. 802-316-5019;

OCT. 11–14: BRATTLEBORO, Brattleboro Literary Festival.Here’s a must-attend event for writers and readers—and a great excuse for leaf peeping in scenic southern Vermont, to boot. Venues throughout town will host readings, panel discussions, and other events with emerging and established authors. 802-365-7673;