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Insider's Guide

These are just some of the unique activities and events Kennebunkport and the surrounding southern Maine coastal areas have to offer in specific seasons. Please don’t hesitate to contact us if you have any questions or would like assistance with your plans. When you arrive at the Inn, we'll have brochures with information on local attractions and suggested driving routes to help you see the most beautiful places along the coast. Enjoy!!

Fall on the Southern Maine Coast

Fall Foliage: Although it varies from year to year, the foliage season in Southern Maine usually begins around the last week in September and continues through the third week of October. Take in the scenery by strolling around the historic district of the Port. Or you could rent bicycles and go for a relaxing and invigorating ride while you explore the local area. If you’d like to see more of Southern Maine, we have maps and suggestions for scenic drives that will show you miles of breathtaking autumn splendor.

Apple Picking: Few activities capture the essence of fall in New England more than apple picking. At Spiller Farm in Wells, you can pick macs, macoun, cortland, honeycrisp, gala, empire, spencer, red delicious, yellow delicious and northern spy, which ripen at different times between late August and mid-October. On the weekends beginning in mid-September, you can also enjoy a farm tour and hay ride and pick-your-own pumpkins.

Annual Wells Chilifest: Chili chefs from all over the known chili universe come to this early September event to inflict pain and suffering on the hungry throngs. If hot chili is not your thing, you can also enjoy crafters and vendors, a car show and live music.

Fall Harvest and Agricultural Fairs: Many annual fairs show off the proud agricultural traditions of Maine and usually take place in the fall to coincide with the harvest.
  • The Cumberland Fair (about 45 minutes from the Inn) at the end of September hosts large exhibit halls, livestock, animal pulling and harness racing, a midway and food vendors, pumpkin contest and pig wrestling competition, among a long list of attractions.
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  • The Fryeburg Fair during the first week in October is Maine’s largest agricultural fair and takes place in a beautiful setting in prime foliage time. Enjoy exhibit halls, flower and craft shows, pie contests, a midway, live entertainment, harness racing, livestock shows, a firemen's muster, and much more. Woodmen’s Day showcases events like bucksawing, chain sawing and tree felling. Fryeburg is located in western Maine, about 2 hours from the Inn. The drive to Fryeburg is very scenic, especially during fall foliage, which makes it a great day trip!
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  • York Harvest Fest (about 30 minutes from the Inn) during the second week in October is a fall festival on the Village Green in the heart of historic York. Good Maine cooking like apple crisp, fish chowder, and baked beans is plentiful. Events include a Native American Pow Wow, kids' fest, antique car show, food festival, puppet show, cider press, craft demonstrations, ox-roast, and tours of the Old Gaol and Jefferds Tavern.
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Jazz at Mast Cove Galleries: Stroll on over for an evening of smooth jazz and blues, surrounded by the fine art collection of the Mast Cove Galleries. Maine's largest privately owned group gallery, Mast Cove continuously exhibits a wide range of subject matter and media, from seascapes in oils and watercolors, to more nonobjective paintings and sculpture.

Summer and Fall Craft Fairs: Throughout the summer and fall, several community organizations host craft fairs, many of them juried, featuring fine quality contemporary art and traditional crafts such as pottery, jewelry, weaving, watercolors, baskets, carvings, photography, handmade toys, herbs, dried flowers and more. Many of these fairs take place on the River Green, across the street from the Inn.

Seashore Trolley Museum: Come and visit the Seashore Trolley Museum, the largest museum of mass transit, where you get to relive history and follow the footsteps of generations past. Spend an afternoon or a day riding our trolleys through the Maine countryside.

All Soul’s Walk: Get in the Halloween spirit with a narrated walk, given by the Brick Store Museum, which will take you through Hope Cemetery to visit the graves and hear the fascinating, and sometimes tragic, tales of early Kennebunk residents. Back at the Museum, you can view the portraits of those featured on the walk.

Christmas Prelude and Other Winter Events

Christmas Prelude: It’s the most wonderful time of the year! This celebration during the first two weeks of December includes three tree-lighting ceremonies, about a dozen Art and Craft Fairs, programs sponsored by the Historical Society, numerous programs of music of the season, and Santa’s arrival by lobster boat. Each year, business people have worked with the community to recreate the spirit and joy of the Christmas season.

Sleigh Rides: Experience the beauty of New England from a Horse Drawn Sleigh! Enjoy a peaceful ride through the woods at Rockin’ Horse Stables. Hot beverages and blankets are provided to keep you warm. Rides are available on weekends only, weather and snow conditions permitting. Private rides are available on both weekdays and weekends; please inquire for more information.

Traditional English Tea: Treat yourselves to a relaxing afternoon at The Tea Room at the English Meadows Inn. Traditional English Tea, complete with homemade scones and sweet treats, is served in their charming Victorian dining room.

February is for Lovers: Throughout the month of February, many restaurants, shops and other businesses in Kennebunk and Kennebunkport are offer something special to celebrate February is for Lovers. At Captain Fairfield, we offer Valentine's Packages throughout February, designed with the details for a perfect romantic escape. Or, choose from our selection of "extras" to customize your getaway.

Winter and Spring Events sponsored by the Historic Inns of Kennebunkport: The Historic Inns of Kennebunkport, of which we are a member Inn, hosts special events exclusively for their guests throughout March and April. Events include Kennebunkport Cookie Madness, Maple Sugar Memories, Historic House Party, English Fudge Tour and Tasting, The Art of Boat Building, and our marqee event, a fabulous Wine Tasting Dinner.

Wine Tastings and Dinners: Throughout the winter and spring, On The Marsh, Cape Arundel Inn, and other local restaurants host periodic wine tastings and wine tasting dinners. These events are designed to illuminate guests about different qualities of the selected wines, the grapes used, the regions they originate from and how they enhance the flavor of certain foods. On a related note, Pier 77 celebrates St. Patrick's Day with a Dinner Dance Party, kicking off their season and revealing an exciting and fresh new menu.

River Tree Center for the Arts: River Tree Center for the Arts has two galleries; the Irvine Gallery features exhibits which may be juried, invitational or in-depth studies of a particular artist, style or medium, and the Performance Hall Gallery is a community exhibition space for two-dimensional work by individuals or community organizations. Both showcase incredibly talented local and regional artists!

Spring in Kennebunkport

Spring Events sponsored by the Historic Inns of Kennebunkport: The Historic Inns of Kennebunkport, of which we are a member Inn, hosts special events exclusively for their guests throughout March and April. Events include Kennebunkport Cookie Madness, Maple Sugar Memories, Historic House Party, English Fudge Tour and Tasting, The Art of Boat Building, and our marqee event, a fabulous Wine Tasting Dinner.

Wine Tastings and Dinners: Throughout the winter and spring, On The Marsh, Cape Arundel Inn, and other local restaurants host periodic wine tastings and wine tasting dinners. These events are designed to illuminate guests about different qualities of the selected wines, the grapes used, the regions they originate from and how they enhance the flavor of certain foods. On a related note, Pier 77 celebrates St. Patrick's Day with a Dinner Dance Party, kicking off their season and revealing an exciting and fresh new menu.

River Tree Center for the Arts: River Tree Center for the Arts has two galleries; the Irvine Gallery features exhibits which may be juried, invitational or in-depth studies of a particular artist, style or medium, and the Performance Hall Gallery is a community exhibition space for two-dimensional work by individuals or community organizations. Both showcase incredibly talented local and regional artists!

Jazz at Mast Cove Galleries: Stroll on over for an evening of smooth jazz and blues, surrounded by the fine art collection of the Mast Cove Galleries. Maine's largest privately owned group gallery, Mast Cove continuously exhibits a wide range of subject matter and media, from seascapes in oils and watercolors, to more nonobjective paintings and sculpture.

Memorial Day Parade: Come celebrate the holiday and the official start of the summer season! The parade proceeds through Dock Square and Lower Village Kennebunk and includes ceremonies in Dock Square and a 21-gun salute at the bridge.

Summer In Kennebunkport

Memorial Day Parade: Come celebrate the holiday and the official start of the summer season! The parade proceeds through Dock Square and Lower Village Kennebunk and includes ceremonies in Dock Square and a 21-gun salute at the bridge.

Kennebunkport Festival: Kick off the summer at the Kennebunkport Festival, a blend of air, music and fine food in the setting of our historic seaside village. Events include privately chefed dinners inspired by artists, a magnificent Twilight Soiree at the St. Anne’s Rectory, Artists in Residence at many Kennebunkport inns, and a Plein Air Painters Invitational. Come celebrate fine art, fine food, fine wine and the art of hospitality.

Summer Theatre: The Arundel Barn Playhouse is housed in an 1800’s farm barn recycled as a live theatre complex. The Playhouse offers live, professional, musical theatre productions throughout the summer. Treat yourself to "an evening in the Mickey Rooney/Judy Garland tradition".

South Berwick Strawberry Festival: The Strawberry Festival, which takes place on the last Saturday in June, features a juried craft show, entertainment, food and strawberry shortcake!

Jazz at Mast Cove Galleries: Stroll on over for an evening of smooth jazz and blues, surrounded by the fine art collection of the Mast Cove Galleries. Maine's largest privately owned group gallery, Mast Cove continuously exhibits a wide range of subject matter and media, from seascapes in oils and watercolors, to more nonobjective paintings and sculpture.

Explore the Shore: The Shoreline Explorer trolley and shuttle system can take you from Kennebunkport all the way down the coast to Wells, Ogunquit and York. You can also travel to the center of Kennebunk. You’ll find the coast to be filled with beaches, lighthouses, shopping and dining, and you can leave your car behind!

Blueberry Picking: Depending on the year, the season for picking Maine blueberries can start just after July 4th and run into September. At Merriland Farm in Wells and Dragonfly Meadow Farm in Arundel, you will also give you a glimpse of the beautiful historic and pastoral areas that can be found as one travels inland from the coast. You can’t get more “Maine” than this!

Fourth of July Celebrations: Kennebunkport is the perfect place to experience this American holiday in small-town, Normal Rockwell fashion. Events include an annual concert and picnic with the Casco Bay Concert Band, which takes place on the River Green, just across the street from the Inn. And no Forth Of July celebration would be complete without fireworks at sunset!

Moxie Day at the Seashore Trolley Museum: Moxie, an edgy, caffeinated beverage invented by a pharmacist in Union, is Maine’s official soft drink. Celebrating Moxie Day in mid-July is a well-established tradition in Kennebunkport. Spend this unique holiday at a very unique museum! The Seashore Trolley Museum is the largest museum of mass transit, where you get to relive history and follow the footsteps of generations past. Spend an afternoon or a day riding our trolleys through the Maine countryside.

Summer and Fall Craft Fairs: Throughout the summer and fall, several community organizations host craft fairs, many of them juried, featuring fine quality contemporary art and traditional crafts such as pottery, jewelry, weaving, watercolors, baskets, carvings, photography, handmade toys, herbs, dried flowers and more. Many of these fairs take place on the River Green, across the street from the Inn.