2019 Boothbay Harbor Region Visitor & Resource Guide

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Events & Specials

Jazz on the Bay

We had the good fortune to meet Molly Pitcher at a fundraiser for our new health clinic in Boothbay this past summer. Molly and her partner, David Clarke, were the highlight of the evening and between listening to this duo play jazz or possibly the wine being freely passed around we found out in the morning that we had won an evening with Molly at the silent auction. Molly and David joined us on the last night of our 2018 season and gave a private concert for our guests in front of a roaring fire overlooking the bay. Susan put out some amazing appetizers, a number of guests added a few adult beverages, and we had the first Five Gables Inn Jazz on the Bay. Molly did a great job and it was such a wonderful night we decided to ask her to join us again this summer. So on May 26, 2019, September 2, 2019 and October 19, 2019 we will be hosting a Jazz on the Bay concert for our guests in the afternoon from 4:00 to 6:00. We hope you can plan a getaway and join us for these special concerts.

Special Five Gables Getaways

We all need more time to recharge and have some fun. A quick getaway to the Five Gables Inn provides the perfect setting and a day at the Botanical Gardens or night at the Boothbay Harbor Opera House rounds out the perfect escape. Call the inn two weeks in advance to book your special getaway and reserve your 1/2 price tickets to either our historic opera House or acclaimed Botanical Garden.

Getaway includes: one nights lodging at the inn, elegant buffet breakfast, afternoon refreshments and homemade treats and two 1/2 priced tickets to either the Coastal Maine Botanical Gardens or night at the Boothbay Harbor Opera House.

Boothbay Harbor Opera House

For generations, the stage of the historic 1894 Opera House in Boothbay Harbor, Maine has played host to actors and musicians from around the state and around the globe. With over 100 events and performances annually, there is almost always something happening at the House-an evening with a Grammy winning musician, a visit from a Broadway actor, nights of jazz or bluegrass, rocking Celtic concerts, lectures, holiday celebrations and community events fill the schedule. With fine acoustics, historic charm and a great old bar room upstairs the Opera House is a gathering place for the local community and visitors alike.

Check out the amazing schedule of entertainment at the Boothbay Opera House and call the inn to reserve your getaway and tickets. 

Coastal Maine Botanical Gardens

A highlight of any trip to the Maine coast is a stop at the Coastal Maine Botanical Gardens in Boothbay. These gardens have become world class and are a major attraction in the Boothbay area. TripAdvisor rated Coastal Maine Botanical Gardens #1 for mid-coast Maine attractions and USA Today named CMBG one of the top 10 (actually 6th) Botanical Gardens in the U.S.

The Gardens has become one of Maine’s top attractions and one of the most distinguished botanical destinations in the country. Its exquisite gardens, dramatic and compelling natural landscape—including nearly a mile of tidal saltwater frontage—make it ever-changing, endlessly captivating and thoroughly unique. As the largest botanical garden in New England, the Gardens comprises 295 acres, 17 of which are gardens featuring native plants of Maine and other plants suited to northern coastal conditions.

Check out what’s blooming and call the inn to reserve your getaway and tickets. 

Events-Local Festivals

Whatever Season, There’s a Reason to Celebrate

Start spring with the glorious bloom of 35,000 tulips at Coastal Maine Botanical Gardens in May, then float into summer with Windjammer Days, a long tradition going back half a century and featuring grand sailing vessels featured in an awe-inspiring Parade of Sail. Our peninsula hosts a number of fun filled festivals throughout the summer and fall, and these festivals provide a fun way to explore our rocky coastline and highlight any trip to the mid coast of Maine. A few of our favorites:

Damariscotta Mills Fish Ladder Festival

May 25, 2019. Alewives are anadromous (sea-run) fish that spend the majority of their life at sea but return to freshwater to spawn. The alewives return each spring and festivities are planned to celebrate this awesome natural event and the restoration of the stone fish ladder, which the fish climb to spawn in fresh water Damariscotta Lake. The festival may be only one day a year, but what a day it will be! As always, the fish will be the main event — it will be possible to view alewives by the fish house, along the fish ladder, in the Williams backyard, and at the top of the ladder.

This year’s festival will be held on Saturday, May 25, 2019 from 10 a.m. to 5 p.m. and kickoff with a 5K foot race earlier in the morning. As before, there will be plenty of food, music and fun for all ages! And of course, there will be ALEWIFE VIEWING up and down the beautifully restored fish ladder!

For more information on the festival or to sign up for the road race check out their calendar.

The Damariscotta Oyster Celebration

June 13, 2019 to June 15, 2019. boasts an oyster culture dating back to 200 B.C!  The communities of the Damariscotta River Region invite oyster lovers from around the world to Maine for the annual Damariscotta Oyster Celebration.

Maine’s Damariscotta River and estuaries produce a unique oyster crop that is recognized around the world for diversity of flavor and quality. The Damariscotta Oyster Celebration was spearheaded by an alliance of Damariscotta oyster farmers to educate and inspire oyster culinary innovations in food, drink, and culture. 

For a fun and tasty weekend check out the schedule for this years Damariscotta Oyster Fest.

The Windjammer Days

June 23, 2019 to June 29, 2019. This festival marks the kick off to summer in our region and is a time to reconnect with family, friends, and neighbors after the long winter, an opportunity to support local businesses and welcome visitors. It is a time to honor our maritime history and celebrate the vital role it plays in the lives of all who live here. Events include grand sailing vessels featured in an awe-inspiring Parade of Sail, the rollicking Cod Fish Race where teams transport a fish through town in full foul weather gear, a street parade, art shows, waterfront concerts, and a spectacular fireworks display.

For more information on this summers official kickoff check out the 2019 Windjammer Days Schedule.

The 8th Annual Boothbay Harbor Fest

August 30th – September 8th, 2019. This is a collection of unique events designed to showcase the creativity of our local business community. This ten-day tradition features Food, Fun & Fashion! Kicking off over Labor Day weekend “A Taste of Local Flavor” is a 3-day adventure for your senses! Weekend Passport includes food tastings and live music at over 15 local restaurants. An unforgettable weekend is guaranteed!

The festival also includes a 5 K Trail Run and Half Marathon. The 5K course winds through one of twenty Boothbay Region Land Trust Preserves on our peninsula. The scenery and natural surroundings are spectacular, and the terrain is well maintained, with little elevation. The Half Marathon is challenging and scenic. Truly a one of its kind in Maine, this course offers miles of water views, from the inner harbor, to open ocean, to lakes and tidal rivers. It crosses over two islands and a historic footbridge.

We are very honored to report that Boothbay Harbor Fest was voted Best of New England Fall Events by Yankee Magazine in 2018. For more information check out this years Boothbay Harbor Fest schedule.

Damariscotta Pumpkinfest

October 12, 2019 to October 14, 2019. 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.
In 2017, Pumpkinfest was delighted to be named Best Fall Festival in Maine by Travel and Leisure magazine!

To learn more about everything pumpkin come join us at this years Damariscotta Pumpkinfest.

Fall Foliage Festival at the Boothbay Railway Village

Every Columbus Day Weekend (October 12, 2019 to October 14, 2019). The Museum’s Village Green welcomes dozens of vendors of handmade items and fabulous food along with a wide variety of live entertainment for the Fall Foliage Festival. The sound of the train’s steam whistle resonating throughout the crisp fall air reminds guests that this is not your typical craft show.

The beautiful crafts are center stage on the Village Green surrounded by the historic buildings and structures of the Boothbay Railway Village. Rides on the narrow gauge steam train and the opportunity for guests to explore exhibits detailing Maine’s railroad heritage, interpreting village life, and displaying more than 60 antique automobiles set this event apart. Artisan demonstrations and live music sponsored by the Boothbay Harbor Memorial Library and the Boothbay Sea & Science Center adds to the fun of this family tradition.

For one of our annual fall highlights mark your calendar for this years Fall Foliage Festival.

The Boothbay Food & Music Festival

Boothbay Food and Music FestivalSeptember. The Boothbay Food and Music Festival started in 2018 is a 3-day event celebrating the very best of Maine’s food, drink, and entertainment. The Festival is organized by local business owners with the generous support of our valued sponsors.

A portion of the proceeds will go to Boothbay Region Community Resource Council, Boothbay Region YMCA, and Boothbay Region Student Aid Fund. More details on this years fun getaway coming soon.

Five Gables Inn A Coastal Maine Bed and Breakfast Inn near Boothbay Harbor