Downeast Excursion Itinerary (3-day)


Note – we put some scheduled times in here just to give you some ideas. You can pick and choose what you want to do. Be sure to look at when they are open and if there are any COVID restrictions. In fact, it would probably be a good idea to call any that you plan to visit just to be on the safe side.

Itinerary Map

Machias River Preserve Trail
Upstream from Machias Bay

This itinerary will take you throughout the Downeast region of Maine, exploring some of the unique and wonderful hikes it has to offer.

Each hike takes place in a separate region of DownEast. While these are just suggestions, feel free to substitute a hike, or otherwise adjust the itinerary to your wants and needs!

Day 1

Night before: Pick your choice of lodging here. We recommend the Barncastle Hotel + Restaurant!

Start the excursion by leaving the hotel and heading to the Osgood Trail that goes up Blue Hill Mountain!

Mountain Road, Blue Hill, ME 04614

This trail will give you extravagant views of the town below, as well as the ocean!

After your hike, have some lunch at Sandy’s Blue Hill Cafe!

40 Maine St., Blue Hill, ME 04614 |207-374-5550

They offer breakfast and lunch throughout the year in a beautiful restored historic house from 1796!

Hours: Thursday-Monday, 8am – 2:00 pm

If you have some extra time before heading to the next time, try out this optional hike on the South Street – Parker Point Trail!

Parker Point Road, Blue Hill, ME 04614

This trail will take you between two points in Blue Hill, so be sure to take into account the return trip. It is an easy trail to end the day with, however!

Leave for hotel in Jonesport. (travel time approximately 1 hour and 30 minutes. Check out local lodging options here.

Day 2

For the first adventure of the day, head down onto Beals Island and then Great Wass Island to the nature preserve.

34 Wildflower Lane, Beals, ME 04611| (207) 729-5181

There, you will find a number of potential trail options, all of which are delightful and serene!

If you are hungry, stop by the Barney’s Cove Lobster Co

7 Wharf Rd, Beals, ME 04611 | (207) 497-2244

“Outdoors..great food…great service….and the view!!!”

Hours: Every day, 8 am-6 pm

If you have some extra time, check out the views around Jonesport! There is a lot to explore and discover.

Once you are finished in the area, head to your next destination, in the Cutler/Machias area! We suggest the Inn at Schoppee Farm for lodging. 21 Schoppee Dairy Road, Machias, ME 04654 | (207) 540-5504

Day 3

While this is a shorter day than the others, there is plenty of time to take in the absolutely gorgeous views of the Bold Coast.

425 ME-191, Cutler, ME 04626

The first stop is the Cutler Bold Coast Trail, one of the most iconic hikes in DownEast Maine. It’s famous for its breathtaking cliffs and outcroppings that are sure to inspire and amaze.

The Cutler Bold Coast Trail is a draining hike at times, so refuel at the famous Helen’s in Machias! The regional staple is a must-visit if you are in the area!

111 Main Street, Machias, ME 04654 | (207) 255-8423

Hours: Sunday 8am – 2pm, Tuesday-Friday 10:30am – 7:00pm, Saturday 7am – 7pm, closed Monday.

This concludes the DownEast Excursion! While there are many more hikes to do in DownEast Maine, these are some of the more notable hikes that give a good diversity of experiences.

Lodging & Dining Alternatives

Packing List


The weather in Maine can be unpredictable. Therefore, here are some ideas to be prepared. Wear comfortable clothes and dress in layers, Maine is very casual, so you probably will not find any restaurants that require formal attire.

Spring/Summer/Fall: clothes, comfortable sneakers or hiking shoes for walking, sun hat, sunscreen, sweater or jacket, insect repellent, toiletries, and phone/camera

Winter: clothes (layers), ski pants highly recommended, winter boots, jacket, hats, scarves, gloves, warm socks, toiletries, and phone/camera. Please pack a helmet if you are participating in snowmobiling, skiing, or snowboarding.

Fun Facts

  • DownEast Maine is full of wonderful hikes! The diversity in environments that DownEast has to offer provides unique views and experiences.
  • The Cutler Bold Coast trail is one of the more famous hikes in the region with its breathtaking views!