Hiker’s Cruise: Portland to Penobscot Bay

While some may wish to hurry from Portland to Penobscot Bay and beyond in one long day, a modestly more leisurely approach will open your eyes to some very scenic, diverse, and interesting diversions that will allow for easy to moderate hiking trails as well as other unique shoreside pursuits, including the majestic Monhegan Island. The itinerary below can be done as shown or split in half and tacked on to either end of a cruise downeast.

Day 1 & 2: Portland to Small Point, Sebasco Estates

Distance: 18.3nm

Sebasco Harbor Resort lies on the western shore of Phippsburg, north of Small Point. Visiting boaters have access to certain of the resort facilities, including a restaurant, swimming pool and golf course, which is convenient if your idea of a hike involves carrying sticks and chasing a little white ball around. The Merritt Mountain trail, a moderate hike of 1.3 miles has its head on the Estates and is one of a number of trails in the area including the Phippsburg Land Trust trails and those around Popham Beach, which is a beautiful sand beach that stretches a good mile in length.

Day 3 Sebasco Estates to Boothbay Harbor, with an optional stop on Seguin Island

Distance: 19.2nm

Seguin Island lies just beyond Small Point and is the site of the second oldest lighthouse on the coast of Maine, commissioned by George Washington in 1795.  The island features five hiking trails, spectacular views and plenty of history.  There are several first come, first served moorings available on the northeast side of the island; anchoring here is not allowed. There is no dock and a landing area that can be tricky at high tide. Be sure to bring tackle to secure your dinghy while you hike.

Boothbay Harbor offers numerous mooring and docking options. Once there, you can stretch your legs by bar-hopping or visiting the numerous attractions in this busy tourist spot. The Boothbay Region Land Trust has an extensive network of preserves, each with trails. Alternatively, you can take a cab ride to the Coastal Maine Botanical Gardens which features a 3-mile network of footpaths.

Day 4  Boothbay Harbor to Monhegan Island to Pemaquid Harbor

Distance: 15.6 nm Boothbay to Monhegan; 13 nm Monhegan to Pemaquid Harbor

Day 4 should start early. Monhegan Island features some truly spectacular trails, the only such trails in the southern and mid-coast area that rival those in Penobscot Bay and points east and it is worth visiting the island for the hiking opportunities alone, if not for the unique charm of this remote outpost. Monhegan should however be planned as a stopover and you should plan to overnight in another harbor. There are a limited number of rental moorings and anchoring in the harbor is inadvisable as the bottom is mostly granite and said to be “littered by 300 years of heavy use.” In addition, even a calm night in Monhegan harbor, where the entrance opens to the prevailing winds, can be rolly. The harbormaster, Sherm, manages the limited number of rental moorings in the harbor and he can be contacted by telephone: (207) 542-9345. If you are lucky and find a mooring you can stay on while enjoying the trails (and a beer or two at Monhegan Brewing) then you have hit the jackpot.

If you are returning to Portland, I suggest an overnight in Pemaquid Harbor which is 13 nm away. Pemaquid Harbor is well protected, and it is possible to anchor in the westernmost part of the harbor, although it is likely that you can find a suitable unused mooring in this area. There is a dock on the south side of the harbor in front of the Contented Sole Restaurant (which I highly recommend for its flatbread pizza and Thursday night live music). This dock also allows you to access Colonial Pemaquid, a reconstruction of a fort dating back to 1692. If you have been successful in trail-walking on Monhegan during the day, this site is worth a visit before setting off on Day 5.

Day 5 Pemaquid Harbor to The Basin

Distance: 27 nm

If you are proceeding farther downeast, Camden lies 38 nm from Pemaquid Harbor. This passage can be broken up with a stop at Port Clyde, Maple Juice Cove, or Tenants Harbor.

 If you are proceeding back toward Portland, the next recommended stop is The Basin on the east side of the New Meadows River which is surrounded by a trail system managed by The Nature Conservancy. The Basin has a narrow entrance that opens into a hurricane hole roughly a quarter mile in diameter where you can securely anchor in mud. Trail access is available by beaching your dinghy on a nearby (rocky) shore with the easiest access point being on Denny Reed Pt. on the southern side of the anchorage.

Day 6 The Basin to Portland

Distance: 21 nm

There are three spots in western Casco Bay that offer modest walks and sites of historical interest, one or more of which could be stops on the return to Portland for a hike and a picnic lunch.

Eagle Island lies off the southern tip of Harpswell Neck and was the summer residence of the famed Arctic explorer Admiral Robert E Peary whose home still sits on the northern point of the island. The home is usually open to the public, although it remains closed in 2024 until storm damage can be repaired. This year you can visit the island by video. The day moorings are not available this year, but dinghies and kayaks can be pulled up on the beach.

Jewell Island, which lies 6 nm east of Portland Harbor, has several miles of easy walking trails and access to a pair of concrete watch towers that were part of Maine’s coastal defense system during World War II. Climbing to the top of these offers spectacular views east to Small Point and Seguin, west to Cape Elizabeth and northwest to Mount Washington. Cocktail Cove on the west side of the island offers a protected anchorage though it can be crowded on weekends.

Fort Gorges lies just outside of Portland Harbor. It is part of a series of similar forts built after the war of 1812 to protect the entrance to Portland Harbor. The area north of the fort provides decent daytime anchoring and a sandy beach for shore access. A walk around the fort will provide an opportunity to stretch the legs and view a structure of historical interest. Get a preview with this video.

If you did not have a chance to visit Portland’s waterfront before you embarked, then you should definitely walk the Old Port area. Portland is also a renowned “foodie” town. It was named Bon Appétit’s Restaurant City of the Year in 2018 and continues to attract diners from all over who come to sample its excellent cuisine and experience its unique charm. The best Portland restaurants are booked weeks in advance even for weeknight reservations, so plan well ahead.