15 Best Things to Do in Winslow (Maine)

With a history stretching back to the 17th century, the area which is now Winslow, Maine played an interesting role in the founding of the nation.

Winslow is in the south-central region of the state. It is near enough to Boston that it was originally settled by an offshoot group of colonists who’d originally planted their roots in the Plymouth Colony.

Due to its proximity to the coast, larger metropolitan areas, and some of the region’s most scenic and undisturbed tracts of inland forests, lakes and rivers, Winslow is the perfect place from which to launch a tour of the area.

Below are 15 things to do in and around Winslow.

1. Fort Halifax State Historic Site

Built in the mid-18th century, Fort Halifax State Historic Site lies along the banks of the scenic Kennebec River and is reported to be the first structure of its kind in the colonies that was built in the blockhouse style.

The term blockhouse refers to the simple, square design that is particularly easy to defend against enemies coming from multiple directions.

Visitors may tour the blockhouse and fortifications; along the way, there are plenty of plaques and exhibits that describe the historical significance of what you’re seeing.

It’s a fascinating and inexpensive look into the past for adults and children alike.

2. Winslow Homer’s Studio

Winslow Homer is considered by many art aficionados and historians to be one of the country’s most important arts.

Homer was born in Boston in 1836 but spent much of his adult life working in his studio in nearby Prouts Neck, where he created many of the works for which he is most well-known.

Guided tours of the artist’s home and studio are available, but probably aren’t a good idea for those traveling with young children.

Tours typically last between two and three hours and aren’t cheap.

The town of Prouts Neck has very limited parking and is often overrun by tourists in the summer months, so if you’d rather avoid that scene, plan accordingly.

3. Colby College Museum of Art

There’s nothing like a free attraction that’s appropriate for the whole family, especially when those hard-earned vacation dollars are disappearing at an alarming rate.

The Colby College Museum of Art is one of the state’s largest and most visited repositories of art; they even offer visitors free audio tours, which are available at the reception desk.

The museum has a permanent collection comprised of multiple galleries, and they offer instructional and educational programs for adults and children as well.

Colby College is located in Waterville, Maine, and guests should plan on spending an hour in the museum to see all that’s on display.

4. Common Street Arts

Also located in Waterville, Common Street Arts is the perfect yin to the Colby College Museum of Art’s yang.

As you may have guessed by the name, it’s more contemporary and less informal and is a hotspot for emerging artists to hone and showcase their skills.

Common Street Arts is part gallery and part communal studio and has become one of the region’s epicenters for art in a variety of mediums.

Located in the Hathaway Creative Center on Water Street, it’s a great place to explore, especially for those interested in contemporary art that’s often more bold and expressive than traditional art from centuries past.

5. L.C. Bates Museum at Good Will-Hinckley

The grounds and buildings that now make up the L.C. Bates Museum at Good Will-Hinckley were once part of a large home for boys and girls who were orphans or came from abusive homes.

The museum is one of those gems that’s not too well-known outside the area, but many visitors count it as one of the highlights of their trip – and one of the most unexpected too.

It’s now on the National Register of Historic Places am=nd sits on a plot of land previously owned by a prominent and wealthy local family.

The items on display are an eclectic mix of world-renowned art and interesting historical tidbits, like a stuffed marlin caught by literary giant Ernest Hemingway.

6. Bigelow Brewing Company

There’s just something about the State of Maine that is conducive to brewing great microbrews. For those with a taste for great beer, a stop at the Bigelow Brewing Company on Hill Road in Skowhegan would be a great way to spend a few afternoon evening or hours.

With homemade, wood-fired pizzas, live entertainment, and an outdoor beer garden, it’s no wonder it’s such a popular place.

Their beer offerings change with the season, and since they offer a wide variety of styles, the likelihood is pretty high that every visitor will find one that fits their taste.

7. Sign of the Sun

Sign of the Sun on Silver Street in Waterville is a favorite place of savvy shoppers looking for unique items not easily found elsewhere. Since it’s not a national mega-retail chain, it’s a great way to support the local economy.

From jewelry and gems to toys and hand-crafted wood, it’s the perfect place to pick up a keepsake or two; their products make great gifts and stocking stuffers as well.

There’s usually an area full of sale and clearance items, and their helpful staff and reasonable prices keep many customers and their children coming back year after year.

8. Frye Mountain State Game Management Area

Covering more than 5,000 acres, Frye Mountain State Game Management Area is pretty expansive by any standards.

It’s located near Montville, Maine, and is full of trails that lead to streams, rivers, and large pine and deciduous forests that are beautiful and peaceful year-round.

There are trails that are appropriate for nearly all ages and levels of physical ability; it’s even possible to get close to the summit of Frye Mountain, which is more than 1,000 feet tall.

The area abounds in animals like deer and foxes, which are the most active in the low light morning and evening hours.

9. Thomas College

Local colleges and universities are great community resources that should be taken advantage of, especially for visitors that are unsure of how they’ll fill their time when exploring a new area.

Thomas College in Waterville was founded in 1894, and its campus is comprised of more than 100 acres, much of which is treed and lies along the banks of the Kennebec River.

An excellent place for a leisurely stroll, they’ve also got a great library and auditorium that hosts live theater, musical performances, and guest speakers throughout the year.

Like most colleges, there are often athletic events going on, many of which are free.

10. Pattee Pond

Located just a few miles outside of Winslow town limits, Pattee Pond is a great place for a morning or afternoon stroll. It’s also got a reputation as a good fishing lake, especially for children and beginners, who appreciate its easily accessible shore and relatively un-finicky fish.

Remember that most game fish are more active on cloudy and overcast days and at dusk and dawn.

Also, keep in mind that each state has its own unique regulations. For those who plan on wetting a line, you’ll need a valid fishing license, whether you’re a Maine resident or an out of state visitor.

11. Riverside Farm Restaurant & Wine Market

Sporting unobstructed and picturesque views of Messalonskee Lake, fantastic food, and a tantalizing variety of wines, Riverside Farm Restaurant and Wine Market is a popular destination for epicureans looking to have their tastebuds spoiled in style.

Many of their wines are locally produced, as are the ingredients used in the majority of their dishes.

The restaurant and wine market have been around for nearly three decades, and have been family owned and operated from the beginning.

There’s an onsite gift shop as well that’s full of handmade arts and crafts, housewares, prepared foods, and baked goods like pies and muffins that are to die for.

12. Lake George Beach State Park

Located near the towns of Belfast and Augusta, beautiful Lake George Beach State Park is accessible via Route 3 and is full of amenities for outdoorsy day-trippers, campers, hikers, and fisherman.

The park’s access fee is inexpensive and provides recreational opportunities regardless of the season.

There are a wide variety of hiking trails leading around the lake and adjacent forest; during winter, they’re great places for snowshoeing and cross country skiing.

The white sand beaches are the perfect places for a summer day of frolicking in the water and catching a few rays with friends and family.

13. New England Sports Camps

For those traveling with children and in need of activities to keep them active and engaged, New England Sports Camps will likely have an appropriate option or two, regardless of their age and athletic ability.

Located on McGrath Pond Road in Oakland, they offer a variety of single and multi-day sports camp options that are led by knowledgeable and enthusiastic coaches.

Many of their programs are offered during the summer months when school isn’t in session, but they offer courses year-round, so check out their website or give them a call to see what’s on their schedule for when you’ll be in the area.

14. Camden Hills State Park

Located in Maine’s Knox County near the town of Camden, Camden Hills State Park is a public area near Penobscot Bay.

The park is full of trails, the most popular of which leads to an elevated bluff that gives guests a panoramic view of the surrounding town, bay, and islands.

Though Maine is full of noteworthy natural scenery, many visitors consider the sights they saw at Camden Hills among the most majestic of their trip, so remember to bring film for your camera or make sure that cellphone has a full charge.

Atmospheric conditions permitting, views of peaks dozens of miles away may be visible.

15. Davidson Nature Preserve

The Davidson Nature Preserve is located on Taber Hill Road in Vassalboro and consists of nearly 100 acres of varied landscape, including a bog, lake, forests, and berry fields.

The town around the preserve was settled in the late 18th century and has a few notable historic attractions that are worth a look as well. But for lovers of nature and idyllic scenery, the nature preserve is the real gem.

During the season, the blueberry fields are open to those interested in spending an hour or two picking their own fruit; it’s a particularly fun activity for those traveling with children.