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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 while 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 Maize at Sherman Farm

September 27 – October 26, 2014
Conway, New Hampshire

12 acre corn maze in Conway, New Hampshire, right over the border from Fryeburg, Maine. Open weekends from Sept. 27 through Oct. 26th, 10am to 4pm. A night time haunted maze is open Friday and Saturday nights in October from 7-9pm. Features hayrides to the pumpkin patch, New Hampshire’s only jumping pillow, and much more.


September 18 - October 4, 2015
West Springfield, Massachusetts (Western Massachusetts)

Celebrate the fall season at The Big E, the largest fair in the northeast. For 17 days during New England’s most colorful season, enjoy free top-name entertainment, major exhibits, The Big E Super Circus, rides, shopping, crafts, parades, and foods from around the world. Take a stroll along the Avenue of States and see impressive replicas of each New England state’s original statehouse sitting on land actually owned by that state. Take a step inside and immerse yourself in the sights, sounds and tastes and of quintessential New England.

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 4-5), Harvest Weekend (October 11-12), Autumn Wagon Ride Weekend (October 18-19) and a Family Halloween (October 26). 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 offers guests a full day of live, interactive entertainment for all ages, including 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.

Salem Haunted Happenings

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 and ready to entertain and amuse you. Guests and local residents just wait 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.

Living Local Harvest Festival

October 2-3, 2015
Martha's Vineyard, Massachusetts

The annual Living Local Harvest Festival brings together the many exceptional people and entities whom work and promote living sustainably on the island of Martha’s Vineyard. The event celebrates and educates on important island issues such as; sustainable agriculture, local food advocacy and education, marine life, renewable energy, resource and land conservation and local living economies. Full schedule of workshops, music and kids activities.

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 2012, the 2,009-pound heavyweight champion became the world’s first 1-ton pumpkin). Come see horse and dog shows, a circus, crafts and farm animals of all kinds.

Jack-O-Lantern Spectacular at Roger Williams Park Zoo

October 2 - November 2, 2014
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.

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 and 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 end 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
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.

Damariscotta Pumpkinfest & Regatta

October 10-13, 2014
Damariscotta, Maine

Come to beautiful midcoast 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 a pumpkin derby.

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.

White Mountain Oktoberfest

October 11, 2014
Loon Mountain – Lincoln, New Hampshire

Celebrate the fall colors with the 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 more than 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 juicy bratwursts, yodeling and folk dance performances, a rousing entertainment lineup featuring die Schlauberger, Spitze!, and more. This year, there will be three Biergartens and expanded outdoor courtyard space for endless amounts of festivities. 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

Columbus Day Weekend marks the 20th Annual Paradise City Arts Festival, a winner of national awards for its extensive selection of fine and functional art of extraordinary quality and diversity. 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 23 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 — or download the brochure here. 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 Celebration

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

Celebrate the arrival of fall with Waterville Valley’s Fall Foliage Fest over Columbus Day Weekend. A weekend of fun family events is planned including kids’ games, pumpkin painting a 5K road race, tent sales, a pie-eating contest and more. Following the 5K run the Fall Foliage Beer Garden will kick off hosting samples of Sam Adams and Harpoon fall brews in the center of Town Square accompanied by live music and a corn hole tourney starting at noon hosted by Harpoon.


October 11 & 25, 2014
Waterplace Park – Providence, Rhode Island

WaterFire is a highly unique public art experience that has attracted tens of thousands of visitors to Rhode Island’s creative capital city of Providence. The event is based on an original artistic installation of bonfires lit on the three waterways passing through downtown Providence. Amidst the flickering firelight of 100 bonfires, stroll through Waterplace Park to enjoy enchanting music and entertainment acts from around the world. (Held select evenings from May-November.)

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.

Plimouth Plantation Sampe Fest

October 11-12, 2014
Plimouth Plantation, Massachussets

Join us for the second annual Sampe Fest as we revel in all things corn with fall-themed activities and yummy corn-inspired dishes. Watch the Miller move the 2,200 pound stone, harness the power of the Town Brook and grind corn. Highlights include: Live music, crafts for kids, hands-on activities, delicious treats from local vendors including cider doughnuts and stuffed cornmeal flatbread sandwiches. Guests can even meet one of Plimoth Plantation’s rare breed goats.

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 18, 2014
Keene, New Hampshire

Keene Pumpkin Festival, the number one vote-getter in the USA Today competition for best specialty food event, returns for its 24th year on Saturday, October 18, in Downtown Keene. 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. At this year’s opening ceremony, dignitaries will acknowledge the return of the World Record for the largest number of lit jack-o’-lanterns, which Keene held for many years before losing it to Boston in 2006. Earlier in the day, the entire family can enjoy special activities for the kids including a costume parade, pumpkin bowling, live music on three stages, face painting, craft booths, lots of food provided by area nonprofits and much more.

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, live music, a road race and the annual Oyster Shuck-Off competition.

Bowen’s Wharf Seafood Festival

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. Café-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 music – folk, Celtic, sea shanties and blues – are just a taste of what you’ll hear. Bring your dancing shoes, because these bands promise to get your feet moving!

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. This year marks the 50th HOCR, with a celebration gala on Saturday evening.

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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