I get this question a lot, “What is there to do in Maine?” or “What is going on in Westport this weekend?” – I decided to include all of Connecticut instead of focusing on Fairfield County. Please feel free to contact me if I left anything event out.
Connecticut
Random ideas
• Attend a Yard Goats game in Hartford
• Watch the sunrise at Compo Beach in Westport
• Spend the afternoon at Captain’s Cove in Bridgeport
• See a concert in Stamford during its Alive at 5 series
• Visit Mark Twain’s house in Hartford
• Bring a picnic lunch at Elizabeth Park in Hartford
• Hike Weir Farm in Wilton.
• Spend the morning at Ambler Farm in Wilton
• Shop downtown Westport
• See a show at the Ridgefield Playhouse
• Have dinner at Little Barn in Westport
• See Irving Berlin at Westport Country Playhouse in Westport
• See a musical at the Godspeed Opera House in East Haddam
• Eat lobster rolls at the Lobster Shack in Westport
• Visit Fort Trumbull State Park in New London
• Eat at Super Duper Weenie in Fairfield
• Visit Old Mistik Village in Mystic
• Watch the Connecticut Sun play at Mohegan Sun
• Explore Gillette Castle State Park in East Haddam
• Visit Harriet Beecher Stowe Center in Hartford
• Drink Fat Orange Cat Brew in East Hampton
• Visit Rosewood Cottage in Woodstock
• Drink at Brewport in Bridgeport
• Visit Castle Craig in Meriden
• Spend the day at the Norwalk Aquarium and Mathews-Lockwood Mansion Museum in Norwalk
• Have dinner in South Norwalk
•Visit Tod’s Point and see the New York City Skyline in Greenwich
• Spend the afternoon at the P.T. Barnum Museum in Bridgeport
• Visit the Nathan Hale School house in New London
• Spend the day at Jennings Beach in Fairfield
• See the New London Ledge Light in New London
• Spend time at Castle Hill Farm in Newtown
• See the sunflowers at Button Hill Farm in Griswold
• Shop on Greenwich Ave in Greenwich
• Take a cruise around the Norwalk Islands
• Eat at Mystic Pizza in Mystic
• See the Glass House in New Canaan
• Visit the Aldrich Contemporary Art Museum in Ridgefield
• Attend the Sheffield Island Clambake in Norwalk (Thursday’s)
• Go on a Hummock Island Oyster tour in Westport
• Attend Shakespeare on the Sound in Rowayton
• Watch a polo match at the Greenwich Polo Club in Greenwich
• Shop the Westport Sidewalk Sale in Downtown Westport in the end of June
• See a movie at the Mansfield drive in
• Spend the day at Sherwood Island State Park in Westport
• Visit Two Roads Brewery in Stratford
Festivals & Fairs
• International Festival of Arts & Ideas in New Haven, June 8-22
• Strawberry Festival, Lyman Orchards, Middlefield, June 15
• North Stonington Agricultural Fair, July 11-14
• Sailfest in New London, July 12-14
• The Craft Festival in Guilford. July 19-21
• Fairfield Sidewalk Sale & Street Fair, Fairfield, July 20
• The Wine Festival in Goshen, July 20-21
• Westport Fine Arts Festival in Westport, July 20-21
• New London County 4-H Expo in July 26-28th
• Windham County 4-H Fair July 26-28
• The Litchfield Jazz Festival in Goshen July 26-28
• Easton fireman’s carnival, Easton, July 30- August 3
• North Branford Potato and Corn Festival, August 2-4
• Middlesex & New Haven County 4-H Fair in Durham August 2-4
• The Holy Rosary Italian Festival in Ansonia August 8-10
• Lebanon Country Fair in Lebanon August 9-11
• Plainville Hot Air Balloon Festival in Plainville, August 23 -25
Maine
Random ideas
• go to a Sea Dogs game
• hike Acadia National Park
• Shop the Old Port in Portland
• Spend the day in Old Orchard Beach
• Have lunch at Portland Head Light
• Visit one of Portland’s many breweries – Bissel Brothers, Allagash, Rising Tide, Mast Landing (Westbrook). Sea Dog, Foundation, Sebago Brewing, Shipyard, and Definitive
• Shop in Freeport
• Hike Wolfes Neck in Freeport
• Eat at Red’s in
• See a show at Thompson’s Point (3rd Eye Blind with Jimmy Eat World in July, Guster in August)
• Watch the sunrise at Spring Point Ledge Light in South Portland
• Take a hot air balloon ride
• Celebrate Auburn’s 150th Birthday
• Go swimming at Range Pond
• Attend First Friday’s in Portland
• Walk Marginal Way in Ogunquit
• Walk downtown Lewiston/Auburn during Final Friday’s.
• See a race at Oxford Plains Speedway in Oxford
• Shop during New Balance tent event in July (remember New Balance is
• Take the ferry from Portland to Peaks Island (especially for the “Mail run“)
• Take the Cat from Bar Harbor to Nova Scotia, Canada
• Tour Henry Wadsworth Longfellow’s childhood home on Congress Street in Portland
• Have a donut at Holy Donut in Portland (other locations on Park Ave and in Scarborough)
• Walk downtown Bath
• Take a Puffin watch cruise from Boothbay Harbor
• Spend the day during the Old Port Festival (I heard this is the final year, June 9th)
• Attend the LL Bean Concert series in Freeport
• Find antiques in Ogunquit
• See Walker’s Point in Kennebunkport
• Go
• Eat at Fat Boys in Brunswick
• Visit Side by Each brewery in Auburn (Coffee and pastries during the morning and craft beer in the afternoon)
• Spend the weekend at Mt. Katahdin and Baxter State Park
Festivals
• The Kennebunkport
• Wicked Good Outdoor Fest, Cumberland, June 15
• Portland Wine Week, Portland, June 17-23
• Maine Whoopie Pie Festival, Dover-Foxcroft, June 22
• Moxie Festival, Lisbon, July 12-14th
• 41st Founders day and Car exhibit, Paris, July 20th.
• Sunday River Touch Mountain Challenge, July 27th
• Maine’s Premier Craft Beer Festival, Fort Preble – South Portland, July 27
• 28th Annual Harpswell Lobster Boat Races – South Harpswell – July 28
• Maine Lobster Festival, Rockland July 31 -August 4th
• Machias Blueberry Festival, Machias, August 16-18
• Blueberry Festival in Rangeley, Rangeley, August 15th
• Great Falls Balloon Festival, Lewiston/Auburn, August 16-18