Weekend Getaways from Boston

Maine sits just two hours from Boston—close enough for a long weekend, far enough to feel like a true escape. The southern coast offers beaches and outlet shopping. Portland delivers urban sophistication with a laid-back vibe. Midcoast harbors invite slowing down. And Acadia provides wilderness within reach.

This guide covers weekend itineraries for every type of traveler, from foodie escapes to outdoor adventures.

The Classic Portland Weekend

Best for: First-time visitors, food lovers, urban explorers Drive from Boston: 2 hours

Friday

Evening arrival: Check into Old Port hotel Dinner: Hugo’s, Eventide Oyster Co., or Central Provisions After dinner: Stroll the Old Port, drinks at Portland Hunt + Alpine Club

Saturday

Morning:

Coffee at Tandem Coffee + Bakery
Walk the Eastern Promenade
Portland Head Light at Fort Williams Park

Afternoon:

Lunch at Duckfat or Highroller Lobster
Portland Museum of Art
Browse Old Port shops

Evening:

Early dinner at Fore Street (reservations essential)
Sunset drinks at Deck (rooftop at Press Hotel)
Live music or brewery hopping

Sunday

Morning:

Brunch at Bayside American Café or Hot Suppa
Portland Farmers Market (Wednesday or Saturday)

Before leaving:

Drive to Freeport, L.L.Bean
Lunch at Harraseeket Lunch and Lobster (Freeport)
Return to Boston by evening

The Beach Weekend

Best for: Families, sun seekers, classic New England experience Drive from Boston: 1-1.5 hours to York/Ogunquit

Friday

Evening arrival: Check into Ogunquit or York area Dinner: Lobster at Barnacle Billy’s (Ogunquit) or The Goldenrod (York) Evening: Stroll Ogunquit village or York Beach

Saturday

Morning:

Breakfast at Amore or Egg & I
Ogunquit Beach (arrive early for parking)
Marginal Way coastal walk

Afternoon:

Lunch at MC Perkins Cove
Beach time or paddleboarding
Ice cream at Rococo

Evening:

Nubble Light sunset (York)
Dinner at Arrows or Earth at Hidden Pond
Ogunquit Playhouse (summer season)

Sunday

Morning:

Brunch at Village Food Market
Short Sands Beach (York)
Explore York Village

Before leaving:

Kittery outlets
Lunch at Chauncey Creek Lobster Pier
Return to Boston

The Acadia Adventure

Best for: Hikers, nature lovers, national park enthusiasts Drive from Boston: 4.5 hours to Bar Harbor

Friday

Afternoon arrival: Check into Bar Harbor or surrounding area Evening: Walk Bar Harbor, dinner at Havana or Galyn’s Sunset: Bar Island walk (check tide tables)

Saturday

Early morning:

Sunrise from Cadillac Mountain (reserve vehicle pass in advance)
Breakfast in Bar Harbor

Morning/Afternoon:

Hike: Precipice, Beehive, or longer Dorr Mountain loop
Jordan Pond House for popovers
Park Loop Road drive with stops

Evening:

Dinner at Burning Tree (local seafood)
Stargazing from the park

Sunday

Morning:

Carriage road bike ride (rent in Bar Harbor)
Thunder Hole and Ocean Path
Sand Beach

Afternoon:

Lunch at Thurston’s Lobster Pound (Bernard)
Bass Harbor Head Light
Drive home via Route 1 coastal route

The Kennebunkport Escape

Best for: Couples, luxury seekers, classic Maine charm Drive from Boston: 1.5 hours

Friday

Evening arrival: Check into boutique inn or B&B Dinner: The White Barn Inn, Bandaloop, or Pearl Evening: Stroll Dock Square

Saturday

Morning:

Sleep in, breakfast at inn
Walk Ocean Avenue to Blowing Cave
Browse Dock Square galleries and shops

Afternoon:

Goose Rocks Beach or Kennebunk Beach
Lunch at The Clam Shack
Spa time at hotel

Evening:

Sunset drinks at The Boathouse
Dinner at Earth at Hidden Pond or Bandaloop
Quiet evening

Sunday

Morning:

Brunch at Duffy’s or Alisson’s
Drive the Ocean Avenue loop
Visit Wedding Cake House

Before leaving:

Cape Porpoise for authentic fishing village
Lobster roll at Nunan’s
Return to Boston

The Foodie Weekend

Best for: Culinary adventurers, farm-to-table enthusiasts Drive from Boston: 2-3 hours (Portland/Midcoast)

Friday

Afternoon: Arrive Portland Evening: Dinner at Fore Street or Hugo’s Late night: Drinks and snacks at Eventide or Central Provisions

Saturday

Morning:

Portland Food Tour or self-guided market exploration
Union Bagel or Standard Baking Co.
Portland Public Market

Midday:

Drive to Midcoast
Red’s Eats in Wiscasset (expect a line)
Continue to Damariscotta

Afternoon:

Oyster tasting (Damariscotta River oysters)
Pemaquid Point Light
Drive to Rockland

Evening:

Dinner at Primo (reservations required far ahead)
Stay in Rockland or Camden

Sunday

Morning:

Breakfast at Rustica (Rockland) or French & Brawn (Camden)
Rockland galleries and waterfront
Camden harbor stroll

Afternoon:

Lunch at Natalie’s or Francine (Camden)
Return to Boston via Route 1

The Outdoor Adventure Weekend

Best for: Hikers, kayakers, active travelers Drive from Boston: 2-4 hours depending on destination

Western Maine Option

Friday: Arrive Bethel or Rangeley Saturday: Hike Tumbledown Mountain or Grafton Notch trails; afternoon kayaking Sunday: Mountain bike or waterfall exploration; return via scenic Route 27

Midcoast Option

Friday: Arrive Camden Saturday: Hike Mount Battie and Mount Megunticook; afternoon sailing or kayaking Sunday: Explore Rockland; hike Ragged Mountain; coastal drive home

Acadia Option

See detailed Acadia itinerary above.

The Winter Ski Weekend

Best for: Skiers, snowboarders, winter lovers Drive from Boston: 3-4 hours to Sunday River/Sugarloaf

Friday

Evening arrival: Check into slopeside lodging Dinner: Resort restaurant or Bethel/Kingfield options Night: Hot tub, early bedtime

Saturday

Full day: Skiing or snowboarding Lunch: On-mountain Evening: Après-ski drinks, dinner at resort or local restaurant

Sunday

Morning: Ski until early afternoon Lunch: Final mountain meal Return: Via scenic Route 26 or 27

Planning Tips

Booking

Peak summer (July-August): Book 2-3 months ahead
Fall foliage (late September-mid October): Book 3-4 months ahead
Off-peak: Often available last-minute
Restaurants: Top spots need reservations weeks ahead

Timing

Leave Friday: Before 3 PM to avoid traffic
Return Sunday: After 2 PM to miss southbound rush
Alternative: Monday departure if schedule allows

Packing Essentials

Layers (weather changes)
Walking shoes
Sunscreen
Rain jacket
Camera
Cash for lobster pounds

Budget Considerations

Save money:

Travel midweek when possible
Book outside peak season
Use vacation rentals with kitchens
Pack picnic lunches
Free activities: beaches, hikes, lighthouse viewing

Splurge on:

One exceptional dinner
Quality lodging (you’re on vacation)
Unique experiences (sailing, puffin tour)

The Perfect Maine Weekend

The best Maine weekend matches expectations to reality. Don’t try to do too much—the two-hour drive from Portland to Acadia can stretch to four with stops. Let one region be enough. Come back for the rest.

Maine rewards those who slow down. The best lobster roll, the perfect sunset, the quiet harbor at dusk—these don’t happen on a schedule. Build space into your weekend. Leave room for the unexpected. The thing you didn’t plan might be the thing you remember.

Whether you’re seeking urban sophistication in Portland, beach relaxation in Ogunquit, wilderness adventure in Acadia, or culinary exploration along the coast, Maine offers the perfect weekend escape. The key is choosing one focus, booking ahead for the essentials, and leaving time to simply enjoy being somewhere that moves at a gentler pace.