1. Kilby House Inn
City: Eastport, ME
Category: Accommodations
Telephone: (207) 853-0989 or (800) 853-45
Address: 122 Water St.
Description: A nicely restored Queen Anne, the Kilby House has five pleasant bedrooms inside. Each has its own unique style and is furnished with antiques and heirlooms, some of which are from the Kilby family who originally lived here. Some have water views, and downtown Eastport is within walking distance. Breakfast is “full,” all right, and the place is an amazing value for what you get—you could set up for a week in Room 4 for the price you’d pay for a single night’s stay in a comparable chamber in parts south.
2. Motel East
City: Eastport, ME
Category: Accommodations
Telephone: (207) 853-4747
Address: 23A Water St.
Description: Sitting just up the road from the downtown, Motel East has the blue expanse of Passamaquoddy Bay as its backyard, and it makes good use of it with broad picture windows in each of its straightforward rooms. Motel fare, but with an inspired vista, Wi-Fi, and easy access to all that Eastport has to offer.
3. Shackford Head State Park
City: Eastport, ME
Category: Parks & Recreation
Telephone: (207) 941-4014
Address: Route 190
Description: Shackford Head is a state park just like Reid or Popham or Sebago Lake, but you’d never know it. In fact, you’d probably never find it, unless you got directions from a kindly Washington County resident. A 90-acre green spot on Moose Island at the far right-hand corner of Maine, the tall headland lifts you up to fantastic views over Eastport after a simple 1-mile walk. But hardly anyone outside of Eastport knows it’s there. The park is tucked away behind the “Boat School” (aka Washington County Technical College) on the edges of the attractive old burgh in a neighborhood where you wouldn’t think to go looking for natural wonders. There it is, though, a woodsy nub with a fantastic prospect, overlooking Cobscook Bay, Lubec, and Campobello. There isn’t much to the place beyond the hill, the woods, and the trails up the mountain and along the shore, but that’s all you need. The hike up the headland is easy, and the vista will knock you out—you can see right out into the salmon pens for which this part of Maine is famous. The trail to the shore is a little more challenging—you have to time it right with the tides—but is equally rewarding. Nice autumn fare, and you’ll most likely have it all to yourself.
4. Waco Diner
City: Eastport, ME
Category: Restaurants
Telephone: (207) 853-4046
Address: Water St.
Description: Don’t let the locals intimidate you away from this legendary diner dive on the waterfront (they like to turn and give newcomers a menacing stare). It actually isn’t even dark and smoky anymore, thanks to a new expansion that has made way for a deck over the water and a face-lift to the exterior (due to its status as an extra in Murder in Small Town X, perhaps?). WaCo stands for Washington County, and this place has been a fixture since the 1920s. Breakfasts are great, and there are all your favorite diner foods from the roast turkey dinner to good burgers. And, of course, plenty of seafood. Open year-round.
5. The Eastport Gallery
City: Eastport, ME
Category: Shopping
Telephone: (207) 853-2965
Address: 74 Water St.
Description: Few Eastport shops have a lot of staying power, but this downtown gallery has been around a while. The 30 area artists represented here are affiliated with the great local Eastport Art Center, and this gallery is where you can buy their work. You’ll find painting, sculpture, and photography. There’s a gift shop as well. Open seven days a week from June through September.
6. Raye’S Mustard Mill
City: Eastport, ME
Category: Shopping
Telephone: (207) 853-4451 or (800) 853-19
Address: Route 190
Description: Eastport’s most famous attraction, Raye’s has been grinding out mustards for more than a century. Their mustards come in more than a dozen flavors, and you can get a gift pack at their Pantry Store. Try the smooth Down East Schooner or the Hot and Spicy. You can also get coffee and a tour of the factory here, and it’s a fascinating slice of Maine history. Open daily from 9 a.m. to 5 p.m. in season.
7. Stage East
City: Eastport, ME
Category: Shopping
Telephone: (207) 853-4747
Address: Washington St.
Description: When this community theater needed seats at its performance space, it went out and bought what it could afford—but the 100 new seats needed repair. So the community got involved, the local vocational school helped fix the hardware, a reupholsterer recovered them, and area residents bought them for $25 each, making it all possible. When they needed still more space, they bought the local Baptist church. This is what community theater is supposed to be about. They do several shows a year, from old standbys to new award winners.