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Letterboxing, Lighthouses and Whale Watching Aboard a Schooner

Program Number: 16269RJ
Start and End Dates:
7/13/2014 - 7/18/2014;
Duration: 5 nights
Location: Eastport, Maine
Price starting at: $999.00 - Price may vary based on date, departure city
Program Type: Intergenerational; Outdoor Adventures, Misc.
Activity Level: t (see description)
Meals: 13; 5 Breakfasts, 3 Lunches, 5 Dinners    
Meal Options: Vegetarian    

Program intended for grandchildren from 8 - 11 years of age.

Make memories with your grandchild in naturally and historically rich Down East Maine as you create adventure in the outdoors through the traditional pastime of letterboxing, with the beacons of the region’s many lighthouses lighting your way. Together, exercise mind and body as you combine elements of orienteering, art and puzzle-solving in an outdoor treasure hunt in pursuit of letterboxes hidden among rocky beaches, fossil beds and hiking trails. Seek out several letterboxes each day, make your own letterboxing stamps and create and hide you own letterbox for future letterboxers to discover. Along the way, explore bogs, a tree farm, a Civil War cemetery and four lighthouses, and go whale-watching aboard a schooner in the Bay of Fundy.


• Your letterbox hunt takes you to the easternmost point of the continental U.S. and into Canada to President Franklin Roosevelt’s summer cottage on Campobello Island.
• Design and create your own distinctive letterboxing stamp and place your own letterbox in the area for others to seek out.
• Visit four of Down East Maine’s iconic lighthouses during the week and step aboard the schooner Ida C. Lore for a whale-watching voyage.

Activity Particulars

Walking 2-3 miles per day over rocky, uneven terrain.

Coordinated by Cobscook Community Learning Center.


A rocky coastline, charming old homes and pristine ocean breezes combine in this memorable port city, an unspoiled harbor of fishing boats and sailing vessels.

One of four B&Bs in Easport's historic district.
Meals and Lodgings
   Eastland Motel
  Lubec, Maine 5 nights
 Eastland Motel
Type: Motel
  Description: The Eastland Motel is newly renovated and immaculate with two beds in most rooms. The motel is managed by owners who are warm and hospitable. This accommodation is a popular eco-adventure destination for lighthouse lovers, kayakers, and outdoor photographers--and boasts bird watching on the grounds.
  Contact info: 385 Coiunty Road
Lubec, ME 04652 USA
phone: 207-733-5501
  Room amenities: All rooms equipped with cable television, free Wi-Fi, and free in-room phone for calls anywhere in the US and Canada. All rooms include a refrigerator, microwave, and coffee maker.
  Facility amenities: Famous home-baked continental breakfast.
  Smoking allowed: No
  Additional nights prior: $75-100 Call for a price quote for additional nights before and after program.
  Check in time: 3:00 PM
  Additional nights after: $75-100 Call for a price quote for additional nights before and after program.
  Check out time: 11:00 AM

Travel Details
  Start of Program:
Sunday, 6:00 pm. You will be staying at Eastland Motel that night.
  End of Program:
Friday, After breakfast You will be staying at Eastland Motel the night before.
  Required documents:
The Participant Information Form is required. A valid US Passport or recognized sovereign national Passport required for attendance on program. Make sure first time or renewing passports is done six months in advance. Check with customs for special provisions for children.
  Parking availability:
There is ample parking at the Eastland Motel
To Start of Program
  Location:  Lubec, Maine
  Nearest city or town:  Machias, Maine
  Nearest highway: Route 189
  Nearest airport:  Bangor, Maine
  From End of Program
  Location: Lubec, Maine
    (Additional transportation information same as above)
Travel Details

Campobello Island


From Airport




Commercial Van/Shuttle
CCLC Shuttle
phone: 207-853-4877
Advanced Reservations Required


Per Person/One Way:


$125 each adult, $75 each child
Prices are subject to change.


Travel Time:


2 hours 




Approximately 100 miles


CCLC will be running a shuttle van from Bangor to Lubec on Sunday, with a return trip to Bangor on Friday. The shuttle will be timed to make sure that you do not miss any part of the program. It will leave Bangor no later than 2:00 pm. on Sunday, and will leave Lubec by 11:00 am on Friday. You will need to contact the program coordinator to arrange for pick up times and locations in Bangor.. Program Coordinator: 207-853-4877.


Eastport, Maine


From Airport




Public Transportation
West's Transportation
phone: 800-596-2823


Per Person/One Way:


$27 (2012price)
Prices are subject to change.


Travel Time:


3.5 hours 


Service runs to/from Bangor once daily, leaving Bangor at 3:15 pm and arriving in Whiting at 6:00 pm. Program coordinator needs to be notified for transport to Lubec (207-853-4877). There is a charge for this service - $20 each way. Return to Bangor is scheduled daily at 10:30 am, arriving in Bangor at 1:15 pm. Requires careful coordination with flight arrivals and departures. For more details, visit

Driving Directions
  Bangor, Maine From Interstate 95 in Bangor take Exit 182A and follow the signs to Bar Harbor and US Route 1, which will put you onto Interstate 395 for three miles. Get off on Exit 4 and follow directional signs to Route 9 (towards Calais). Turn right off the exit ramp and follow signs for Route 9. Travel approximately 70 miles and turn right onto Route 192 to Machias. In Machias, turn left onto US Route 1. Travel approximately 17 miles into Whiting, where you will make a right onto Rt. 189. Follow 189 to Lubec where you will find the Eastland Motel on your left as you arrive in Lubec.
  From the South via Route 1 Travel north on US Route 1. Travel through the towns of Ellsworth, Machias, into Whiting where you will make a right onto Route 189. Follow Rt. 189 and follow it into Lubec. You will find the Eastland Motel on your left as you approach Lubec.
Equipment Requirements: A lightweight backpack to carry extra layers of clothing and your letterboxing supplies is necessary. A water bottle is a necessity. Collapsible hiking poles are helpful, but certainly not required. If you already have a letterboxing journal, please bring it. If you would like a special journal for all of your letterboxing, you should bring a journal, about 5x7 (approximately) with unlined pages. We will make small journals for those who do not bring their own.
The prices listed for commercial services and facilities that are not included in the program cost, such as airport shuttles or extra nights lodging, are subject to change without notice. Since Road Scholar cannot guarantee the accuracy of these prices, we strongly suggest contacting the companies directly for the most up-to-date information.

Daily Schedule

Day 1: Arrival and registration/Orientation
(Sunday, July 13)
 Afternoon: Check into the Eastland. Program Coordinator will deliver welcome packets the motel...
 Dinner: Welcome dinner at a waterfront Lubec restaurant.
 Evening: Orientation with program coordinator and lead instructor to go over program activities.
Accommodations: Eastland Motel
Meals Included: Dinner

Day 2: Letterboxing Workshop/Picnic/Letterboxing Hunt in Lubec and Trescott/Beach Picnic
(Monday, July 14)

Note: We cover trails in the Trescott and Lubec trails, scouting out letterboxing while enjoying the scenic splendor of Cobscook Bay.

 Breakfast: Breakfast will be served at the spacious Eastland lobby. Bring your appetite!
 Morning: Travel by vans to the Cobscook Community Learning Center (CCLC) for workshop on Letterboxing. Discuss basic letterboxing etiquette, rules, history, and definitions. Students will design and make their own distinctive letterboxing stamps. They should give some thought to stamp designs that say something unique about themselves. Originality is encouraged. A visit to the Letterboxing North America website prior to your Down East visit ( might be of interest. All materials for stamp construction will be provided.
 Lunch: A picnic lunch will be enjoyed at the Cobscook Community Learning Center.
 Afternoon: Test your exploration skills as we pursue the letterboxes of Lubec and Trescott. We'll test our skills at our first lighthouse at West Quoddy Head Museum and State Park,. exploring rocky beaches and hiking trails.
 Dinner: Enjoy a beach cookout at Commissory Point, feasting on grilled chicken, hot dogs, and corn on the cob and much more around a cozy beach campfire.
Accommodations: Eastland Motel
Meals Included: Breakfast, Lunch, Dinner

Day 3: Letterboxing Hunt/Picnic/Letterboxing Hunt on Canadian Campobello Island
(Tuesday, July 15)

Note: Explore two lighthouses, hike wooded trails, bogs and coastlands.

 Breakfast: Enjoy a nutritious and home-baked continental breakfast at the Eastland.
 Morning: Vans will depart from the Eastland at 9:00. In our quest for new letterboxes, we'll head across the Bay for Campobello Island where we'll visit another lighthouse, Head Harbor Light, (also known as East Quoddy Head Light). This is one lighthouse we will actually get to enter, but the tides have to be timed just right. We'll hone our map-reading skills and work on some good old puzzle solving.
 Lunch: Enjoy a picnic lunch on the beaches of Campobello Island.
 Afternoon: We'll explore the Canadian island and the Roosevelt Cottage International Park. We'll visit shorelands and bogs. We'll search for letterboxes with historical value and those located in a scenic wonderland. And, before we leave the island, we'll visit another lighthouse, Mulholland Light, which guards the channel between Lubec and Campobello Island.
 Dinner: We'll enjoy a hearty home-cooked spaghetti dinner with the members of the community and learn about some local history.
 Evening: Experience the color of a lobsterman's life through the eyes of his wife and business partner.
Accommodations: Eastland Motel
Meals Included: Breakfast, Lunch, Dinner

Day 4: Letterboxing Hunt/Whale Watching Aboard Schooner/The Hunt Continues in Eastport
(Wednesday, July 16)

Note: Drive around the Bay to catch the tide for a schooner ride and explore Eastport's letterboxes

 Breakfast: Breakfast will be served at the Eastland's roomy lobby. Bring your appetite.
 Morning: Vans will depart the for Eastport at 9:00 a.m. At the Eastport breakwater we'll catch a ride on the 108' schooner Ida C. Lore and head out Head Harbor Passage for a whale watching excursion that is sure to show us porpoise, seals, seabirds, and hopefully, a whale or two. You'll be amazed at the rapidly changing tides.
 Lunch: You can explore Eastport for lunch on your own. Consider a lobster roll at Quoddy Bay lobster, hot dogs at Rosie's (the best hot dogs on the coast of Maine), or a quiet lunch on the dockside Chowder House.
 Afternoon: After lunch we'll head to the Pottle Tree Farm in Perry, where we will walk a labrinth, visit a medicine wheel garden, and utilize an actual outdoor classroom while we seek out the secret letterboxes of the forested wonderland.
 Dinner: Enjoy a private supper party at an Eastport location. We can't tell you more. Some things are more fun if you don't know all the details.
Accommodations: Eastland Motel
Meals Included: Breakfast, Dinner

Day 5: Letterboxing the trails of Cobscook State Park and Bell Mountain
(Thursday, July 17)

Note: We'll see more woodlands and coastal overviews.

 Breakfast: Enjoy hearty home-baked fare at the Eastland.
 Morning: Vans will depart from Lubec heading for Cobscook State Park, a beautiful seaside park with several letterboxes hiding along the trails. Don't miss the one one the overlook. We'll also visit Bell Mountain with an unusual set of letterboxing directions.
 Lunch: Enjoy a picnic lunch on a spectacular lookout at Cobscook Bay State Park.
 Afternoon: Enjoy a few hours of free time this afternoon. Seek out some boxes on your own or discover some of Lubec's attractions that you may have missed earlier.
 Dinner: A lobster feast will be served at a seaside restaurant overlooking the Lubec Channel.
 Evening: Graduation fun and festivities
Accommodations: Eastland Motel
Meals Included: Breakfast, Lunch, Dinner

Day 6: Bid farewell to new found friends.
(Friday, July 18)

Note: Explore a location for our new letterbox.

 Breakfast: A farewell breakfast with your new friends.
 Morning: Enjoy Lubec and catch all of the things you may have missed during the week.
 Afternoon: Bid a fond farewell to new found friends. Have a safe journey home and come back and visit us anytime.
Meals Included: Breakfast
Important information about your itinerary: Every effort has been made to ensure the accuracy and completeness of the information featured on this website. Itineraries are based on our best information at this time. Circumstances beyond our control may require us to adjust itineraries or other details. We regret any inconvenience this may cause and appreciate your understanding. Information will be sent to you from your Program Provider approximately three weeks prior to the program start date. The prices listed for commercial services and facilities that are not included in the program cost, such as airport shuttles or extra nights lodging, are subject to change without notice. Since Road Scholar cannot guarantee the accuracy of these prices, we strongly suggest contacting the companies directly for the most up-to-date information.

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