How to Plan an Epic Guys' Weekend in Maine
Every friend group has talked about it:
"We should plan a guys' trip."
Then life gets busy, schedules get complicated, and another year passes.
Whether you're planning an annual reunion, celebrating a milestone birthday, organizing a bachelor party, or simply reconnecting with old friends, Maine offers the perfect combination of outdoor adventure, great food, craft beer, golf, and relaxation.
Here's how to plan a guys' weekend everyone will actually remember.
Step 1: Pick the Right Destination
Not every Maine destination offers the same experience.
• Bethel & Sunday River Area
Best for:
- Golf groups
- Bachelor parties
- Outdoor adventures
- Groups wanting a large private home
• Portland
Best for:
- Brewery enthusiasts
- Food lovers
- Walkable nightlife
• Bar Harbor
Best for:
- Scenic coastal experiences
- Acadia National Park
Step 2: Build the Weekend Around Shared Experiences
The best trips aren't packed with activities. They're built around memorable moments.
Popular options include:
• Golf
A morning round followed by lunch and drinks.
• Breweries
Explore local craft breweries and taprooms.
• Hiking
Choose a trail that fits the group's fitness level.
• Sports & Games
Cornhole tournaments, poker nights, fantasy football drafts, or arcade competitions.
Step 3: Stay Together
Large groups often default to hotels.
But a private vacation home offers:
- Shared gathering spaces
- Fire pits
- Hot tubs and saunas
- Fully-equipped kitchens
- Game rooms
- Spacious living rooms for movie nights
- Large private yards for outdoor games
Step 4: Leave Room for Downtime
Many planners make the mistake of over-scheduling.
Build in time for:
- Morning coffee on the deck
- Watching the game
- Hanging out around the fire pit
- Relaxing in the hot tub
Why Sunday River & Bethel Is One of Maine's Best-Kept Secrets
For groups seeking mountain views, championship golf, breweries, outdoor adventures, and luxury lodging, the Sunday River and Bethel area consistently delivers.
One of its biggest advantages is accessibility. Your crew can easily reach Bethel with a scenic drive from Boston, Portland, and much of New England. For those flying in, it's approximately 90 minutes from Portland International Jetport and about 3.5 hours from Boston Logan Airport—close enough for a long weekend, yet far enough to feel like a true escape.
Unlike crowded city destinations centered around bars and nightlife, Bethel offers something increasingly rare: room to breathe. Days can be spent on the golf course, mountain biking, hiking, paddling, or exploring local breweries. Evenings are best enjoyed around a fire pit, in a hot tub, or sharing stories with friends under the stars.
It's the kind of destination that turns a simple golf trip into an annual tradition.
🐝 Looking for a Place to Stay Near Sunday River?
Check out Hideaway Havens, two stunning chalets located just 2 minutes apart in a peaceful mountain neighborhood, only 12 minutes from Sunday River Resort and minutes from Bethel Village restaurants and shops.
The homes sleep 13 and 16 guests separately, or up to 29 guests combined.
Enjoy Amenities Like:
🌄 Panoramic mountain views
🛁 Private hot tubs + cozy barrel saunas
🔥 Fire pits for s’mores nights
🍖 Gas BBQ grills for gourmet cook-outs
🎮 Arcade games, pool table, ping pong & air hockey
🎤 Karaoke setups for unforgettable family nights, and much more....
Perfect for:
- Multi-family vacations
- Ski trips
- Summer adventures
- Fall foliage weekends
- Family reunions
- Retreats & group getaways
Looking for a memorable mountain escape?
What’s your favorite activity near Sunday River? We’re always looking for new adventures for our next Maine trip! 🌄
Frequently Asked Questions
Where is the best place for a guys' weekend in Maine?
Popular destinations include Bethel, Portland, Bar Harbor, and the Moosehead Lake region, depending on the group's interests.
What should you do on a guys' trip?
Golf, brewery visits, hiking, fishing, mountain biking, sports viewing, poker nights, and group meals are all popular activities.
Is Sunday River, Maine good for group vacations?
Yes. Sunday River, Maine offers a wide variety of outdoor recreation, dining, and vacation rentals ideal for groups.
Jeana Deninger
Jeana Deninger
Jeana Deninger
Jeana Deninger