American Dream Trip
Portland, Maine

Road-trip guide · Maine

Portland

A road-trip stop through Maine.

Photo via Wikipedia — Portland, Maine

Plan with AI

Discover your perfect Portland

Looking for places to stay, eat, or explore?

What travelers do here

Things to do in Portland

Portland Head Light, Cape Elizabeth
Old Port district walk
Old Port District, Portland
Allagash Brewing Company tour
Maine Historical Society & Wadsworth-Longfellow House
Portland, Maine — Old Port District
Eventide Oyster Co. — Portland, ME
Portland Head Light, Fort Williams Park

Overnight

Where travelers stay

Lodging 1

Bayley's Camping Resort, Scarborough, ME

Lodging 2

Hampton Inn Portland-Downtown/Waterfront

Lodging 3

The Press Hotel, Portland

Lodging 4

Hotel in Old Port via Booking.com

Pulled from real itineraries built on American Dream Trip.

Want it done for you?

Grab a hand-curated guide

Love this plan? Our premium itineraries go deeper — vetted stops, timing, and local secrets, ready to download and take on the road.

Real trips

Trips that visit Portland

Real road-trip plans built by other travelers on ADT.

Carolina to Acadia: A Fall Foliage RV Loop with Dogs, Lobster, and Family Stops

10 days, first-time RVing, two dogs, and the best of Vermont, New Hampshire, and Maine in late October

Vermont & Maine: Farms, Factories, and Back Roads

A 5-day Sunday-to-Thursday loop through Green Mountain creameries, maple sugarhouses, and Maine's coast — with an early start, early evenings, and a proper splurge night

Vermont & Maine Off-Season: Farms, Factories, and Fog-Swept Lighthouses

A 7-day round trip from Rome, NY through Vermont's dairy country and Maine's working coast — post-foliage, pre-crowds

Vermont & Maine Off-Season: Farms, Factories, and Foghorns

A 7-day New England loop from Rome, NY — cheese, cider, lighthouses, and lobster with none of the leaf-peeper crowds

Salem Spells & Boston Streets: A Girls' Trip Through New England's Most Iconic Cities

Halifax to Salem to Boston — History, Haunts, and High-End Shopping for Two Best Friends

Shawshank to Acadia: A Fall Foliage Road Trip from Chicago to the Maine Coast

10 Days | Chicago → Mansfield OH → Bangor ME → Bar Harbor → Portland ME → Salem MA → Chicago

Lobster, Lighthouses & Lazy Coves: Maine Coast Road Trip

Bay City, MI → Kennebunkport → Portland → Rockland → Camden → Bar Harbor and back — 10 days of pure Maine coastal magic

Acadia or Bust: A Father-Son Road Trip from Florida to Maine

10 Days · Blue Ridge Parkway · Shenandoah · Acadia National Park · Beehive Trail & Beyond

Acadia or Bust: A Father & Son Road Trip from Florida to Maine

10 Days • Lakewood Ranch, FL to Acadia National Park, ME • Tent Camping & Truck Bed Adventure

Acadia or Bust: A Father & Son Road Trip from Florida to Maine

1,400 Miles, Epic Hikes, Lobster Rolls, and Memories That Outlast the Sunburn

Nearby

Other cities in Maine

All road trips through Maine →

Ready to map yours?

Plan your Portland road trip

Free AI-built itinerary in about 90 seconds. No credit card, no signup.

Plan my road trip →