Have you ever considered visiting Windsor? Or perhaps not even heard of it? Portland, Kennebunkport, and Bar Harbor are most likely, but Windsor, Maine probably sounds as foreign as the sun is to England in January. The Windsor Fair is what makes it famous every August, but there are more fun things to do in Windsor Maine, too.
As far away as Windsor is from where I call home today, my family finds time every year to return to Maine. It has taken living everywhere else in the world to truly appreciate the simplicity and quirkiness of my hometown roots: Windsor, Maine.
What To Do In Windsor Maine From A Local
After spending 2 weeks in the heart of Windsor this spring, when Mainers flock to warmer weather or hit spring skiing in the Colorado slopes, and wait for mud season (or snow) to pass, I’ve decided my hometown deserves a post about things to do in Windsor, Maine. It’s not typically found on a New England bucket list but with these unique spots, it should.
For a visitor, finding most things to do in Windsor are limited to Trip Advisor. And while that’s great that the web returns results, the problem is that most of those things aren’t REALLY in Windsor.
So, as a tribute to this hard-working 2600 population town and my duty as the former Windsor Fair Maine Apple Queen (which I will forever get teased about), here’s what you need to know about making the most of Windsor – any time of the year.
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Where Is Windsor?
Windsor is nestled between the state’s capital, Augusta, and a popular coastal town, Rockland. It’s a pass-through town for most commuters and big trucks.
With the exception of August, when Windsor is host to Maine’s second-largest agricultural fair, the rest of the year is fairly quiet.
8 Things To Do In Windsor Maine
Whether you’re visiting Maine and just driving through or renting a camp on one of Windsor’s charming lakes, here are 9 things to make your visit to Windsor, Maine a wicked good one.
1 – Visit Hussey’s General Store
If a visit to a General Store in Maine is on your bucket list, then THIS is the one to go to. Hussey’s sells everything you could imagine. But it’s not just the inside of this store that makes them famous. It’s their signature sign that simply states they sell guns, wedding gowns, and cold beer that does.
Hussey’s Famous General Store Sign
The store sign has been used for CD covers by bands all over the country. It’s so popular in fact that people reach out to ask me if Hussey’s with the guns, wedding gowns, and cold beer sign is the same store I talk about when I go to Maine. Why, yes!
The thing about Hussey’s that I love is that my kids love it, too. It’s a family favorite thing to do in Windsor Maine. We indeed buy cold beer, fishing bait, and pretty much everything else, too. The only thing missing from our cart is a paper bag full of penny candy Swedish fish that I used to fill up during every visit to Hussey’s as a little girl.
Even without the penny candy jar, Hussey’s has done a great job at filling my Maine void. I stock up on wicked whoopies, homemade Maine blueberry bismarks, and the cutest Maine clothes I have ever seen. And a bonus is that Hussey’s is a YETI dealer.
Hussey’s General Store
With food this good and sweaters this cute, you can spend hours getting lost in this 3-story Maine general store.
2 – Go Antiquing At Elmer’s Barn
Technically this is in Coopers Mills, Maine but since it’s right on the town line I’ve always considered it a part of Windsor. Our big yellow school bus drove by it to pick up kids when I attended Windsor Elementary School, so it’s understandable why I consider it a part of Windsor turf.
The funny thing is, until this spring trip, I had never stepped into Elmer’s Barn. Literally, within 2 miles from the house I grew up in, I never considered it a thing to do, a place to explore, or a fabulous resource for shopping.
I always marveled at the curious antiques lying around in the front yard, its massive sign, and the unusual things it hung from the front porch.
Elmar’s Barn Antiques
After all these years I discovered what I was missing!
Elmer’s Barn hosts 50 vendors over 3 floors. You’re guaranteed to be surprised, find a wickedly cool gift, and likely get lost.
For farmhouse decor or any person seeking a one-of-a-kind, Elmer’s Barn is a place to visit while driving through or visiting Windsor. From colorful Maine buoys to rustic Maine apple crates, this place is full of wicked unique treasures.
3 – Go “Upta Camp” On Our Personal Favorite, Three Mile Pond
If you overhear anyone talking about going “upta camp”, it means they are heading to a lake house. Imagine Maine Cabin Masters, and that’s 100% what upta camp is. It took ages for my California husband to eliminate images of me pitching a tent to spend “summah upta camp” as a little girl.
Maine lingo takes a while to understand, but then once you catch on, you realize just how wicked good it really is.
And camp life in Maine is awesome. Seriously. It’s where Disney based the Parent Trap and where internationals alike send their kids for the summer. Check out Camp Kieve and Camp Kippewa.
If I could update the Maine slogan, there’d be a little camp on the corner of the “Way Life Should Be” sign as you cross the New Hampshire border.
Most people visit Maine in the summer, but time on the water is awesome all year round. Mainers know it and nearby states are buying up properties as soon as they go up for sale.
Favorite things to do in Windsor Maine on Three Mile Pond include:
- Paddleboarding
- Boating
- Fishing, including ice fishing
- Eagle watching
- Loon listening
- And our family favorite, the sunsets!!! They are simply AMAZING.
Upta camp on Three Mile Pond
You can rent a camp on Three Mile Pond otherwise the nearest hotel is in Augusta.
4 – Experience The Windsor Fair
Windsor is home to the great Windsor Fair the last week of August.
This agricultural fair, formerly focused on the apple, was established in 1888 and going ever since. Though grandstands aren’t as full as they used to be, the Windsor Fair offers a week-long agenda for adults and children of all ages.
Our personal favorites at the Windsor Fair include betting on horse races, watching the pig scramble, joining the women’s pan-throwing contest, buying out the squirt gun game for 20+ of us, and enjoying more homemade lemonades, doughboys, and clam platters than my family can shamefully count.
But if the lights and betting aren’t your things in August, the grounds themselves are interesting to check out when the fair is long gone.
During the off-season, visit the fairgrounds to witness what “jogging a horse” means or to just get a glimpse of one of many four-legged residents. This beauty here put on a private show for my daughter and me during our visit this spring.
The Windsor Fair
The Windsor Fairgrounds is home to different events throughout the year. On a lunch stop at Rideout’s or a shopping spree at Hussey’s, check for event signs inside that might be taking place during your visit.
5 – Go Apple Picking At Bailey’s Apple Orchard
Go apple picking at Bailey’s Apple Orchard. Rather than drive through the main roads of Windsor, drive along Hunts Meadow Road to visit this tucked-away farm.
Grab a ladder and pick your tree. They offer different varieties and everything you need to enjoy the taste and colors of fall.
Bailey’s isn’t open all year round so check their hours before you go.
6 – Order A Chicken Basket At Rideout’s Market & Grille
Located at the intersection of Route 17 and Route 32, Rideout’s is not just for refueling. They are the perfect place for lunch on your way to Camden, Pemaquid or to take upta camp. Seriously good, this place puts a chicken basket on the map next to The Red Barn. So why drive another 12 miles when you can just eat here?
This is what my chicken basket would look like if I hadn’t eaten it so fast. But seriously, it really is just like The Red Barn chicken.
Red Barn Chicken, Augusta Maine
And if chicken isn’t what you crave, then try their haddock basket or ask if they have a chowder special. Looking for a side? The chicken with bacon and ranch pasta in the cooler is to die for!
Then head over to the cash register and check out all the homemade goods. Toss in a classic whoopie pie, raspberry Bismarck or blueberry muffin and you’ll be in Maine food heaven.
7 – Indulge In A Seafood Platter At Aunt Gin’s [CLOSED]
Update 2023: Sadly Aunt Gin’s Restaurant is no longer in business.
I flew all the way from England to end up at Aunt Gin’s.
This isolated restaurant on Route 17 doesn’t look like it boasts a 3-page menu but the packed parking lot every day all day says it all.
From their signature gin cocktails to their seafood platter for 2, Aunt Gin’s is the perfect place for a sit-down meal. Each room inside is named a different surrounding town with themes, including a large fish tank, to keep the kids entertained.
Aunt Gin’s
Stop by for a drink at the bar or for a three-course meal. Aunt Gin’s doesn’t disappoint and I hear their Friday and Sunday buffets are quite amazing, too!
8 – Grab Breakfast At Priscilla’s Diner
If you enjoy experiencing diners, like famous Moody’s Diner, then grab coffee and breakfast at Priscilla’s.
Formerly the Windsor Diner and been around for years, this is a local hotspot for breakfast. Scoot across the street after filling up at Rideout’s Market & Grille.
Final Thoughts On Things To Do In Windsor Maine
Despite Windsor not looking like much from the outside for most travelers driving through, this little town is packed with fun things to do for everyone.
From an old-fashioned diner to shopping at Hussey’s or Elmer’s Barn to adventures at the Windsor Fair or on Three Mile Pond, Windsor Maine offers several unique things to do. You can purchase your own Windsor t-shirt, too!
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So, the next time you’re driving to Augusta, Rockland, or considering a first-time visit to Maine, consider having a blast with these wicked good things to do in Windsor, Maine.
Looking for more travel ideas? Try these.
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