Highland Lake is different. It doesn't have the frantic energy of Sebago or the commercial weight of the coast, and tucked right on its eastern shore is a place called Tarry-A-While Resort. Honestly, if you’ve driven through Bridgton, you might have missed it. That’s sort of the point.
The resort feels like a time capsule. It dates back to the mid-19th century, originally serving as a summer estate before transitioning into the hospitality icon it is today. When you pull up, you aren't greeted by a sterile lobby or a digital kiosk. You get 25 acres of pines, a sprawling lawn that slopes toward the water, and a view of Pleasant Mountain that looks like a painted backdrop. It’s quiet. So quiet you can hear the loons from the porch of the Main Inn.
People come here for the "resort" experience, but it’s not the Sandals version of a resort. It’s the Maine version. That means creaky floorboards, the smell of woodsmoke, and a private beach where the sand is actually sand, not crushed gravel.
The Reality of Staying at Tarry-A-While Resort
Most people looking at Maine vacations get sucked into the Bar Harbor vortex. They spend $500 a night to fight for a parking spot at a trailhead. Tarry-A-While is the antithesis of that chaos. The property is split between the Main Inn, several individual cottages, and the Hedges—which is a separate building with its own vibe.
The Main Inn is where the history lives. If you’re a fan of Victorian architecture but hate the "stuffy museum" feel, you’ll dig it here. The rooms are simple. They aren't trying to be ultra-modern boutique hotel suites with glass showers and mood lighting. They are comfortable, clean, and feel like your grandmother’s very nice lake house.
But let’s talk about the cottages. This is where the resort actually shines. If you're traveling with a family or a group of friends who actually like each other, these are the play. They vary in size—some are tiny one-bedroom setups like "The Studio," while others like "The Lodge" can hold a small army. You get a kitchen. You get a porch. You get the ability to wake up, make coffee, and walk twenty feet to the water without seeing another soul.
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What You’re Actually Doing All Day
What do you do here? Basically nothing. And everything.
The waterfront is the heartbeat of the place. Highland Lake is incredibly clear. Because Tarry-A-While has its own private beach, you aren't dealing with the crowds at the public Woods Pond or the Bridgton town beach. They provide canoes, kayaks, and rowboats. If you’ve never tried to row a heavy wooden boat across a glassy lake at 6:00 AM while the mist is still rising, you haven't lived. It’s a workout, but it’s basically therapy.
There is a golf course right across the street. The Bridgton Highlands Golf & Country Club is literally a stone’s throw away. Even if you aren't a "golf person," the views from the holes there are some of the best in the Oxford Hills.
Eating (and Drinking) Near the Lake
Food is a big deal here, though it's changed over the years. Historically, the resort was known for its Swisstel restaurant—a nod to the Swiss heritage of former owners. Today, while the dining scene in Bridgton has exploded, Tarry-A-While remains a place where breakfast is the star.
- The On-Site Vibe: It’s casual. You aren’t dressing up for dinner.
- Bridgton Proper: You’re only a few minutes from downtown Bridgton. You’ve got places like Beth's Kitchen Cafe for a massive sandwich or Vivo Country Italian for something a bit more upscale.
- The Picnic Strategy: Most regulars at the resort just hit up Hannaford in town, stock their cottage fridge, and grill out. There is something about eating a burger on a paper plate while watching the sunset over Pleasant Mountain that beats a five-star meal every time.
Why Highland Lake Beats the Big Names
Size matters, but bigger isn't always better. Sebago Lake is massive, sure. But it’s also full of massive boats. It gets choppy. It gets loud.
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Highland Lake is roughly four miles long. It’s manageable. It’s intimate. At Tarry-A-While Resort, you’re positioned perfectly to catch the afternoon sun. The water stays warm well into September, which is a secret most "leaf peepers" don't realize. If you come in the fall, you get the foliage reflected in the lake, but you can still actually go for a swim without getting hypothermia.
The Logistics Most Guides Skip
Let’s get into the weeds. Traveling to Western Maine requires a car. Don’t try to Uber here from Portland; it’s a 45-to-60-minute drive, and you’ll never find a ride back.
Parking at the resort is easy and free, which is a rarity these days. WiFi? It exists. Is it fast enough to stream 4K movies while three people are on Zoom calls? Probably not. But honestly, if you're coming to a 19th-century lake resort to work on a spreadsheet, you’re doing it wrong. Cell service is decent but can be spotty depending on your carrier once you get deep into the trees.
One thing to keep in mind: accessibility. Because these are historic buildings, there are stairs. Lots of them. If you have mobility issues, you’ll want to talk to the staff specifically about which cottage or room fits best. They are incredibly accommodating, but the terrain is "Maine flat," which means it’s actually a bit hilly.
The Local Perspective
Bridgton isn't just a tourist trap. It’s a working town. When you stay at Tarry-A-While, you’re part of a community that supports the local cinema (the Magic Lantern is a must-visit) and the local bookstores.
There’s a specific kind of person who returns to Tarry-A-While year after year. It’s the person who wants their kids to experience the world without a screen for a week. It’s the couple that wants to read books in Adirondack chairs until the sun goes down. It’s not about "amenities" in the corporate sense. It’s about the amenity of silence.
Actionable Steps for Your Trip
If you're planning to book, keep these specific tips in mind to get the most out of the Highland Lake experience:
- Book the "shoulder" season. Late June or the week after Labor Day offers the best balance of weather and price. July is beautiful but it’s the busiest time for the resort.
- Bring your own gear. While they have boats, bring your own fishing tackle. Highland Lake is known for smallmouth bass and chain pickerel.
- Plan a "Mountain Day." Pleasant Mountain (home to Shawnee Peak/Pleasant Mountain Ski Area) is just down the road. Hike the Ledges Trail for a panoramic view of the entire Lake Region. It’s a moderate climb but the payoff is huge.
- Check the events. Bridgton often has "Art in the Park" or local farmers markets. Ask the desk when you check in; they usually have a printed flyer of what’s happening in the Oxford Hills that week.
- Pack for the temperature swing. Even in July, Maine nights can get chilly. Bring a heavy sweatshirt for the bonfire. You’ll need it.
Tarry-A-While Resort isn't trying to be the next big thing. It’s quite happy being the "old thing" that works perfectly. If you want a place that feels like home—if home was a sprawling estate on a crystal-clear lake—this is where you end up. Just don't tell too many people. We’d like to keep the peace and quiet just as it is.