30 days in Williamstown & Greater Portland & Casco Bay Itinerary

30 days in Williamstown & Greater Portland & Casco Bay Itinerary

Created using Inspirock United States trip planner

Plan created by another user. Make it yours
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Williamstown
— 11 nights
2
Bailey Island
— 6 nights
3
South Portland
— 11 nights

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11
nights
Williamstown

Williamstown
Williamstown is a home-rule-class city in Grant and Pendleton counties in the U.S. Ark Encounter has been added to your itinerary. Get out of town with these interesting Williamstown side-trips: Midway (Damselfly Gallery & Equus Run Vineyard & Winery), XhilaRacing (in Florence) and The Ridge Winery Tasting Room (in Vevay). There's still lots to do: sample the fine beverages at Buffalo Trace Distillery, experience rural life at Old Friends at Dream Chase Farm, indulge your thirst for a good beer at Woodford Reserve Distillery, and admire the majestic nature at Clifty Falls State Park.

To see where to stay, reviews, traveler tips, and tourist information, you can read our Williamstown route planner.

Portland to Williamstown is an approximately 7-hour flight. You can also drive; or do a combination of bus, train, and taxi. Traveling from Portland in February, things will get somewhat warmer in Williamstown: highs are around 44°F and lows about 25°F. Wrap up your sightseeing on the 12th (Wed) to allow time to travel to Bailey Island.

Things to do in Williamstown

Parks · Museums · Breweries & Distilleries · Wildlife

Side Trips

Find places to stay Feb 1 — 12:
Highlights from your plan
Ark Encounter
Ark Encounter
Buffalo Trace Distillery ©
Buffalo Trace Distillery
Sun Valley Farm ©
Sun Valley Farm

6
nights
Bailey Island

Bailey Island ©
Venture out of the city with trips to Freeport (Freeport Historical Society, Fiore Artisan Olive Oils & Vinegars, &more).

To find where to stay, traveler tips, and more tourist information, refer to the Bailey Island route maker.

Use the Route module to find suitable travel options from Williamstown to Bailey Island. Traveling from Williamstown in February, things will get slightly colder in Bailey Island: highs are around 35°F and lows about 16°F. On the 19th (Wed), you're off to South Portland.

Things to do in Bailey Island

Parks · Outdoors · Nature · Wildlife

Side Trip

Find places to stay Feb 12 — 19:
Highlights from your plan
Wolfe's Neck Woods State Park ©
Wolfe's Neck Woods State Park
Bailey Island Bridge ©
Bailey Island Bridge
Maine Beer Company ©
Maine Beer Company

11
nights
South Portland

South Portland ©
South Portland is a city in Cumberland County, Maine, United States, and is the fourth-largest city in the state, incorporated in 1898. Explore the numerous day-trip ideas around South Portland: Grist Mill Park (in Yarmouth), Peaks Island (5th Maine Museum & Richard Boyd Art Gallery) and L.L. Bean Factory Store (in Freeport). The adventure continues: walk around Bug Light Park, don't miss a visit to Liberty Ship Memorial, sample the tasty concoctions at Fore River Brewing Company, and wander the streets of Old Port.

To see maps, ratings, reviews, and more tourist information, go to the South Portland travel planning site.

Getting from Bailey Island to South Portland by journey takes about 1.5 hours. In February, plan for daily highs up to 35°F, and evening lows to 16°F. Cap off your sightseeing on the 1st (Sun) early enough to go by car back home.

Things to do in South Portland

Parks · Outdoors · Trails · Museums

Side Trips

Find places to stay Feb 19 — Mar 1:
Highlights from your plan
Portland Head Light ©
Portland Head Light
Bug Light Park ©
Bug Light Park
Old Port ©
Old Port

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