We are a Registered Maine Guide service based in Oakland, Maine, and we get asked the same question by almost every client who travels in for a trip: what else is there to do around here?
Plenty, as it turns out. Oakland sits at the bottom of the Belgrade Lakes chain, ten minutes west of Waterville and about twenty minutes north of Augusta. It is a small mill town with a big lake on its western edge, and it makes a genuinely good base for a few days in Central Maine. Here is what we actually point people toward.
Start with the water: Messalonskee Lake
Messalonskee Lake — almost everyone local calls it Snow Pond — forms Oakland’s western boundary and is the lowest lake in the Belgrade chain. It runs roughly nine miles, glacially carved, narrow at the northern end and opening out wide toward the south.
It is a genuinely versatile piece of water. Anglers come for largemouth and smallmouth bass and for pike. Paddlers favour the calmer northern section, where headway-speed rules keep things quiet. The marshy southern end toward Belgrade is the wildlife end: eagles, loons, terns, kingfishers and warblers all work that shoreline.
There is a public boat launch, and it is worth knowing that it fills up quickly on summer weekends — get there early, or plan a weekday. If you did not tow a boat up, there are rental outfits on the lake.
Our take: if you want to fish it properly without burning a day working out where the fish are, that is exactly what our guided lake and pond trips are for.
Winter is not the off-season
This is the part visitors underestimate. Oakland does not shut down when the lakes freeze — it changes gear. Ice fishing on Messalonskee and the wider Belgrade chain typically runs from January into March, depending on the year, and hard water season is one of the best times to be here.
The town leans into it too. Oakland Recreation runs the Seekins Kids Ice Fishing Frenzy on the first Sunday in February, which is a good, low-pressure way to get children onto the ice.
One honest caution: ice conditions vary enormously from year to year and from cove to cove. Never take someone else’s word for ice thickness, including ours in a blog post written months ahead. Check it yourself, or go out with someone who does this for a living — which is what our guided ice fishing trips exist for.
Trails and dry land
- Messalonskee Stream Trail — an easy walking and birdwatching path right in town, following the stream that once powered Oakland’s mills.
- Kennebec Valley Trail — a converted rail corridor nearby, good for walking and biking with very little elevation to fight.
- Mount Phillip — a short, popular loop over in Rome with a summit view out across the Belgrade Lakes. This is the one to do if you only have a couple of hours.
Town events worth planning around
Oakland Recreation keeps a busy calendar for a town this size. The regulars include:
- Summer Concert Series — Thursdays at the Gazebo, June through August
- Summer Movie Series — outdoors at Pleasant Point Park
- Easter Egg Hunt — the Saturday before Easter, split by age group
- Trunk or Treat — the Sunday before Halloween at Messalonskee High School
- Tree Lighting — the first Friday in December
Dates and details shift from year to year, so check the town’s recreation page before you build a trip around one.
Big music just over the town line: Bowl in the Pines
This one surprises people. About ten minutes from Oakland, at 1 Geranium Lane in Sidney, is Bowl in the Pines — an open-air amphitheatre with a shell stage and capacity for more than 7,000, which makes it one of the largest open shell outdoor stages in the country. It is operated by the Snow Pond Center for the Arts.
Programming runs from local artists and festivals through to nationally touring acts, comedy and tribute shows, generally across summer into early fall. If your trip lands in season it is worth checking what is on before you finalise dates — an afternoon on the water followed by a show in the pines is a hard evening to beat.
Waterville, ten minutes east
Oakland is small on purpose. When you want more, Waterville is right there, and it carries the groceries, the hospital, Colby College and the I-95 interchange.
Worth a stop:
- Colby College Museum of Art — a serious collection of American art, and an easy hour indoors if the weather turns.
- Front & Main — comfort food built around Maine farms and coastline.
- Amici’s Cucina — Italian; pasta, seafood and steaks, with gluten-free options.
- Holy Cannoli — downtown bakery and cafe for scratch pastries and a decent lunch.
A little local history
Oakland was a manufacturing town long before it was a lake town. Mills powered by the falls on Messalonskee Stream turned out axes, scythes and other edge tools through the nineteenth century, alongside woolens. If that is your kind of thing, the Oakland Historical Society keeps the local record, and you can still read the industrial bones of the town as you walk the stream.
Where to stay
Oakland runs to small, characterful lodging rather than resorts:
- Pressey House — a bed and breakfast in Oakland near Messalonskee Lake, which publishes a useful local travel guide of its own.
- My Valhalla Farm — a historic farmhouse bed and breakfast with a pool.
- Chain hotels in Waterville, ten minutes away, if you would rather trade character for convenience.
If you are coming specifically to hunt or fish with us, look at our lodging page first — we can usually point you at something that matches the trip and the season.
Hunting: WMD 16
Oakland sits in Wildlife Management District 16. Confirm your zone on the MDIFW district descriptions. Our deer hunting trips and turkey hunts both work this country, and we run nuisance wildlife removal here year-round.
Making a trip of it
The short version: Oakland gives you a nine-mile lake, quiet trails, a genuine small-town events calendar, a 7,000-seat amphitheatre one town over, and a small city ten minutes east — without the coastal crowds or the coastal prices.
We guide here year-round, which is the whole reason we know the place this well. If you want to build a trip around any of it, take a look at our fishing trips, hunting trips and recreational trips, or just get in touch and tell us what you want to do.
Sources and further reading
This guide draws on the following, all of which are worth reading directly — particularly for current dates, hours and prices, which change:
- Oakland, Maine — maine.com. Background on the town, the lakes and its mill history.
- This Gorgeous Maine Lake Just Outside Waterville Is A Local Favorite — Ever After in the Woods. Detail on Messalonskee Lake, its access and its wildlife.
- Recreation Events — Town of Oakland. The official events calendar; check here for current dates.
- Bowl in the Pines — Sidney, Maine. Venue details and the current season’s line-up.
- Travel Guide — Pressey House, Oakland. Local restaurant and attraction recommendations.
We are not affiliated with any of the businesses or organisations listed above, and none of these are paid placements. They are simply the places we would send a friend.