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New England Events – October 2014

Early to mid October is peak foliage time in New England – a perfect time to explore winding roads to see the spectacular yellows, oranges and reds on the way to one of these New England events. See specific websites to confirm dates and times, associated fees and parking information. Note that some highly popular events may need advance ticket purchases.

For more New England events in October, check the individual state websites at the bottom of the page.


The Fryeburg Fair – Maine’s Blue Ribbon Classic!

September 28 - October 5, 2014
Fryeburg, Maine (close to North Conway, New Hampshire)

Come to the largest agriculture fair in Maine – eight days of entertainment and education for the whole family.  See a variety of livestock, draft show horses and ponies, pulling horses and oxen, sheep dog trials and a huge parade on Saturday. There’s a thrilling midway with amusement rides and delicious food, live music all day and nightly entertainment. The Fair attracts upwards of 300,000 visitors each year.  There are 3,000 campsites onsite.


Special Weekends at Billings Farm & Museum

Weekends through October
Woodstock, Vermont (Central Vermont)

Visit a working dairy farm and a tribute to the rural way of working life in Vermont amidst autumn splendor.  Throughout October, special events are a part of the experience including a Pumpkin & Apple Celebration (October 5-6), Harvest Weekend (October 12-13), and Autumn Wagon Ride Weekend (October 19-20). Across the street, visit the Marsh-Billings-Rockefeller National Historical Park.  Tour the estate and walk through one of Vermont’s most beautiful landscapes, under the shade of sugar maples and 400-year-old hemlocks, across covered bridges and alongside rambling stone walls.


King Richard's Faire

August 30 - October 19, 2014
Carver, Massachusetts

King Richard’s Faire is New England’s largest and longest-running Renaissance Festival. Tucked away on 80 acres of beautiful, enchanted forest off Rt. 58 in Carver, Mass., King Richard’s Faire now begins to prepare for its 34th season offering guests a full day of live, interactive entertainment for all ages, including new liger cubs, daring knights jousting on horseback, and eight stages filled with song and dance, stunts and storytelling. Every Saturday afternoon, the King’s Stage offers special themed contests and events to add variety to the festival-like entertainment lineup.


Haunted Happenings, Salem

The month of October
Salem, Massachusetts (North of Boston)

A month-long festival in the bewitching seaport of Salem includes a series of spooky events that involve haunted houses, storytelling tours and a Grand Parade.  A favorite October destination because of its infamous Witch Trials of 1692, Salem was once a major maritime hub for the New England colonies and is rich in history and culture. This highly walkable city is also accessible by ferry from Boston (seasonally).


Return of the Pumpkin People

The month of October
Jackson, New Hampshire (White Mountains Region)

This is the month that the Jackson Area of New Hampshire is populated with dozens of “Pumpkin People” and/or “Pumpkin Animals” all dressed up ready to entertain and amuse you. Guests and local residents wait just for this event to start every fall season in which pumpkins are used as the heads of figures. You will find Pumpkin People at local inns, businesses, restaurants, attractions and even private homes.  Whatever these Pumpkin People do this year, you will want to catch them in the act.


The Topsfield Fair

October 3-13, 2014
Topsfield, Massachusetts

This event is the quintessential country fair – traditional agriculture, big entertainment, rides, games, shopping, and great food… something for everyone! Established in 1818, America’s oldest continuously running agricultural fair opens with the famed New England Giant Pumpkin weigh-off (in 2007, the 1,689-pound heavyweight champion earned a place in the Guinness Book of World Records!).  Come see horse and dog shows, a circus, crafts and farm animals of all kinds.


National Cranberry Festival

October TBD
Carver, Massachusetts

Edaville’s annual National Cranberry Festival is back by popular demand. Featuring all things cranberry, this two-day event offers excitement and education for the whole family. An artists’ marketplace of handmade goods and seasonal delights will beckon you to stroll the grounds. Enjoy live music, dog agility, Irish step dancing, and giant bubble play. Get up close with the cranberry in its natural environment, and then get in depth with its history in our one-of-a-kind Cranberry World Museum. Helicopter rides, pony rides, and much more!


Jack-O-Lantern Spectacular at Roger Williams Park Zoo

Throughout October - check website for specific dates and times
Roger Williams Park Zoo - Providence, Rhode Island

Hailed by USA Today as “extraordinary.” Experience the glow of 5,000 pumpkins carved into amazing works of art and set in a magical display during this night-time Spectacular. A team of professional pumpkin carvers spends six weeks creating the trail, resulting in a truly breathtaking display.  Feast your eyes on thousands of carved and illuminated pumpkins with hundreds of them depicting people, places, and scenes — all with painstaking detail and amazing intricacy!


Southington Apple Festival

October 3-5 and 10-12, 2014
Southington, Connecticut

This annual festival is a family-oriented community event spanning the first two weekends in October. The event offers six days of spectacular fun, delicious food, live entertainment and crafts.  Come see the Apple Fritter and Apple Pie Eating Contest, plus an Apple Harvest Bed Race, road race and more.


Damariscotta Pumpkinfest & Regatta

October 4-13, 2014 (see full schedule on website closer to the date)
Damariscotta, Maine

Come to beautiful mid-coast Maine for a celebration of all things pumpkin. This festival is a fun-packed week of events including a pumpkin paddle boat relay and pumpkin motor boat regatta, pumpkin polo, and the Maine Pumpkin Growers Organization-sanctioned giant pumpkin weigh-off.  There’s also pumpkin catapulting, a pumpkin drop,  underwater pumpkin carving, a giant pumpkin parade, 60 giant pumpkins lining Damariscotta’s main street, and the first annual pumpkin derby.


OctoberFest at Harpoon Brewery

October 3-4, 2014
Harpoon Brewery, South Boston Waterfront

Harpoon Brewery’s annual German-style OctoberFest boasts 3 stages with live music, a big selection of Harpoon beers and ales, and lots of German food sold by a local restaurant.  Come do some Chicken Dancing, keg bowling and enjoy the German Oompah bands at one of New England’s largest OctoberFests.


Vermont Artisans’ Open Studio Weekend – Statewide

October 4-5, 2014
Statewide (website offers map)

Most Vermont craftspeople work in studios located in or close to their residences. These are places of production and inspiration located in downtowns as well as at the ends of dirt roads. Wherever their locations, they are exciting places to visit because they reflect the dynamic yet organized process that is used to produce the finished work of art. On this special Open Studio Weekend, drive through the beautiful countryside of Vermont and visit these artists.  See website for a map of participating artists.


North American Wife Carrying Championship

October 11, 2014
Sunday River Resort – Newry, Maine

Fun for competitors and thousands of spectators alike, the Wife Carrying Championships receive international media attention each year.  Teams from across the United States and Canada compete head-to-head for fame, fortune and a chance to compete at the World Championships in Finland. The origin of North American Wife Carrying Championship is based in Finnish history. The modernized wife carrying event is all in fun, and in reality, is a true test of physical strength, agility and teamwork between man and woman.


Acadia's Oktoberfest Food & Crafts Festival

October 10-11, 2014 (tentative)
Acadia National Park – Southwest Harbor, Maine

The first day of this special weekend will open with an afternoon and early evening “Wine & Cheese Tasting’ accompanied by music. Maine wine distributors will offer wines from around the world and Maine cheese makers will serve exciting pairings of specialty cheeses. ‘A BREWFEST TO REMEMBER’ will be held October 6. This event has been noted as “one of the spots not to miss” and one of the “top ten festivals in New England” by the national RV Magazine and New England brewery magazines, respectively.


Stowe Foliage Art Festival

October 10-12, 2014
Stowe Events Field - Stowe, Vermont

Fall is Festival time in Vermont and Stowe celebrates the absolute zenith of foliage color with the Stowe Foliage Arts Festival. 200 juried artisans exhibit and sell a wide range of contemporary and traditional craft work as well as original Art, photography, sculpture, and specialty food products. While having a bite and a beer in the dining tent, enjoy live music on Saturday and Sunday. All in all, spending a day at the Stowe Foliage Arts Festival is a great way to enjoy Vermont during its most glorious season.


Oktoberfest at Loon Mountain

October TBD
Loon Mountain – Lincoln, New Hampshire

Celebrate the fall colors with all Alpiner Oom-Pah Band, German music, German food, and German beer. There is no charge to enter the event; food and beer is a la carte. Prepare for sauerkraut, stew, strudel, bratwurst and knockwurst. Various games will be setup on the lawn for some friendly competition. The Adventure Center is open for mountain bike rentals and tours, the climbing wall and the bungee trampoline. Visitors can also experience the trails and foliage on horseback or head to the Summit on the gondola.


Massachusetts Annual Cranberry Harvest Celebration

October 11-12, 2014
Wareham, Massachusetts

This fun family event features juried crafters, activities for children, animal shows, cooking demonstrations, food vendors, pony and wagon rides and much more. The highlight of the day is an opportunity to witness a working cranberry bog. Please, no pets. Last year’s event was attended by over 32,000 visitors.


Connecticut Garlic & Harvest Festival

October 11-12, 2014
Bethlehem Fairgrounds – Bethlehem, Connecticut

Garlic lovers unite! Visit garlic cooking demonstrations, stay for a live band performance and learn how to grow garlic at informative lectures. Many garlic dips, spreads, cheeses and oils will be available for purchase from garlic specialty food vendors – most offering FREE samples to try before you buy! Stop by the produce stands for fresh garlic and a variety of other fall produce. When you’re hungry, venture over to the food court.  Homemade roasted garlic sausage with peppers and onions, garlic marinated steak sandwiches, garlic roast pork sandwiches, deep fried garlic and garlic ice cream are just some of the items you’ll find! Bring the kids for some fun with rides and games.


Newport's International Oktoberfest!

October 11-12, 2014
Newport Yachting Center – Newport, Rhode Island

This bona fide Bavarian weekend bubbles over with an expanded International Biergarten, juicy bratwursts, yodeling and folk dance performances, a rousing entertainment lineup featuring die Schlauberger, SPITZE!, The Alex Meixner Band, The Austrian Boys Band and more. A kid-friendly Kindergarten area rounds out fall’s choice festival as a place for the whole family to sample Oktoberfest’s multitude of flavors. All held along the beautiful Newport waterfront.


Paradise City Arts Festival

October 11-13, 2014
3 County Fairgrounds - Northampton, Massachusetts

Meet 275 of the nation’s very best craftsmen and artists showing their newest work. Dine on sensational cuisine by Northampton’s best chefs under the Festival Dining Tent. Catch the excitement of live performances by nationally and regionally acclaimed musicians. Ranked #3 among all art and craft fairs nationwide, it’s an experience like no other – beautiful, unique, festive and fun!


Cape Ann Artisans Fall Studio Tour

October 11-13, 2014
Cape Ann, Massachusetts (north of Boston)

This self-guided tour along the scenic coastline of Gloucester and Rockport presents a unique opportunity to meet fourteen professional artists and see their work in the setting in which it was created. The work represented includes: pottery, painting, sculpture, photography, mosaics, fiber art and jewelry. Several of the artists will be demonstrating their working process during the tours. Brochures with route maps will be available at the Cape Ann Chamber of Commerce, the Rockport Information Booth on Rte 127, on the Cape Ann Artisans web site and at each of the artisans. A bright magenta Studio Tour banner will mark each location. Many studios are open year round.


Chowder Days at Mystic Seaport

October 11-13, 2014
Mystic, Connecticut

In the crisp New England air, enjoy unforgettable clam chowder and other fresh seafood specialties, along with seasonal desserts and beer, wine and apple cider. Stroll through our village and enjoy live music. Bring the kids to enjoy a “clammy” art project and story time in the Children’s Museum. Or, climb aboard our steamboat Sabino for leaf-peeping from the water.


Waterville Valley Fall Foliage Festival

October 11-12, 2014
Waterville Valley Town Square – Waterville Valley, New Hampshire

To complement the brilliant fall foliage, Waterville Valley has scheduled a weekend of family activities, free outdoor concerts, pie-eating contest, 5K road race, tent sales and more!


Quilting in the Land of Milk & Honey

October 11-12, 2014
Middlebury, Vermont

This is our 5th biannual quilt show, this year featuring quilt artist Anne Standish. There will be about 90 quilts on display, including a N.H. quilt shop’s quilts (Keepsake Quilting — well known through their catalog and website ) called Keepsake Quilting’s Challenge Collection; Quilts of Valor — quilts made to honor our soldiers and go to them after they have been displayed; and vendors, basket raffles, a raffle quilt (shown on our website), consignments, and lunch.


Dummerston Apple Pie Festival

October 12, 2014
Dummerston Congregational Church - Dummerston, Vermont

Come see Vermont at its best – choose from 1,500 pies made in the historic Dummerston Congregational Church, homemade ice cream, fresh donuts, hot cider, Green Mountain Coffee, and Grafton cheese. Or maybe have some of each! Pies available whole or by the slice. Worship at 9 am surrounded by pies. Fire Department Breakfast, Grange Lunch. This is a favorite event of region motorcycle groups who make a day of it…search online for details.


Keene Pumpkin Festival

October 17-19, 2014
Keene, New Hampshire

The sun starts to set and hundreds of volunteers rush to light thousands and thousands of carved pumpkins. Visitors from around the world watch the dark become illuminated by nearly 30,000 votive candles. Earlier in the day, the entire family can enjoy special activities for the kids including a costume parade, a seed spitting and pie eating contests, live music on three stages, face painting, craft booths, lots of food provided by area non-profits and much more. The evening ends with a spectacular fireworks display.


Annual Wellfleet Oysterfest

October 18-19, 2014
Wellfleet, Massachusetts (Cape Cod)

This two-day family festival celebrates the town’s famous oysters, clams and shellfishing traditions and brings together locals and visitors alike for a weekend full of hometown flavor and big time fun! There is something for everyone: local cuisine, arts and crafts, educational programs, cooking demonstrations, children’s activities, walking tours, theatre, live music, a road race and the annual Oyster Shuck-Off competition.


Bowen’s Wharf Seafood Festival - Newport, Rhode Island

October 18-19, 2014
Newport, Rhode Island

Honoring the “Harvest of the Sea,” the Bowen’s Wharf Seafood Festival offers copious amounts of seafood, continuous live music, and family fun, all beneath the Wharf’s colorful tents. Neighboring restaurants and fisherman’s associations serve up their most celebrated seafood dishes (lobster dinners, clam chowder, stuffed quahogs, clam cakes, shrimp, scallops, raw oysters and clams, as well as a few dishes for landlubbers and kids). Spirits and soft drinks are available. Desserts include tempting pies, ciders, and other baked goods. Cafe-style seating is set up throughout the Wharf. As you fill your bellies with fresh dishes, sit back and enjoy the beats from area bands. Under the music tent, live folk, Celtic, sea shanties and blues music are just a taste of what you’ll hear. Bring your dancing shoes, because these bands promise to get your feet moving!


Harvest Celebration! Johnny Cake Festival

October 18-19, 2014
South Kingstown, Rhode Island

Make sure you don’t miss this unique harvest celebration with over 75 local vendors including area farms, artisans and restaurants.  Savor an abundance of food and beverages including Johnny Cakes (a cornmeal cake that is a local favorite), Clam Cakes, chowder, wine and more.  Enjoy tours of Kenyon’s Grist Mill, the oldest manufacturing business in Rhode Island; Kenyon’s is best known for their Stone Ground White Corn Meal or “Johnny Cake Meal”.  There will be live music, demonstrations, and a variety of samples along the Queen’s River and waterfall.


Head of the Charles Regatta

October 18-19, 2014
Boston / Cambridge, Massachusetts

Head Of The Charles® Regatta, the world’s largest two-day rowing event, was first held on October 16, 1965. The race was established by the Cambridge Boat Club members with the advice of Harvard University sculling instructor Ernest Arlett.  Arlett proposed that a “head of the river” race similar in tradition to races held in his native England, be held on the Charles River. “Head” races, a class of regattas, are generally three miles long — boats race against each other and the clock, starting sequentially approximately fifteen seconds apart. Winners of each race receive the honorary title of “Head of the River” or, in this case, “Head Of The Charles.” Today, more than 7,500 athletes from around the world compete in 55 different race events. The Regatta grew to a two-day event in 1997 and now attracts up to 300,000 spectators during the October weekend.


Harvest on the Harbor

October 22-25, 2014
Portland, Maine

At this three-day event, you’re sure to find more than one event to whet your appetite. There is something for everyone: the Grand Tasting on the Harbor, the Maine Lobster Chef of the Year Competition, seminars and cooking demonstrations, a marketplace with all things food related, and much more. Fees: $35 & up. Many of these events are extremely popular and sell out quickly – be sure to buy tickets early online!


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