🥾 ActiveWeekend · from Boston, MA
Acadia Gateway & Downeast Coast
Acadia National Park on Maine's Mount Desert Island is the crown of the New England coast — Cadillac Mountain at 1,529 feet is the highest point on the US Atlantic seaboard, and the park's 45 miles of historic carriage roads provide world-class cycling through birch and spruce forest. Day two follows the Downeast coast through the fishing villages of Ellsworth and Blue Hill.
Day 1 — Bar Harbor, MEDay 2 — Blue Hill Peninsula, ME
Day 1 — Bar Harbor, ME
Day 1 — Bar Harbor, ME
🚗 4 hr 45 min driving📍 5 stops
🌅
Morning
🚗
Drive
Boston, MA → Acadia National Park
4 hr 30 min8:00 AM → 12:30 PM
Drive north via I-95 and US-1 through Portland, Brunswick, and Ellsworth to Mount Desert Island.
Cadillac Mountain Summit
The 3.5-mile South Ridge Trail ascends 1,529 feet to the summit of Cadillac Mountain, the highest point on the US Atlantic coast north of Rio de Janeiro. The summit is above treeline for the final mile; the 360-degree view encompasses Frenchman Bay, the Porcupine Islands, and on clear days, the highlands of Nova Scotia. From October through March, the summit sees the first sunrise in the continental US.
12:30 PM📍 See location
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Lunch
🚗
Drive
Cadillac Mountain → Jordan Pond House
15 min1:30 PM → 1:45 PM
🍽️ Lunch1:45 PM
Jordan Pond House
A National Park Service restaurant in operation since 1870, serving the park's signature popovers — hollow, light rolls the size of softballs, baked to order — on a lawn facing Jordan Pond and the Bubble Mountains. The tradition of afternoon tea and popovers at the Pond House has continued through every era of the park's history; the current building dates to 1979 after the original burned.
4 options · tap to switch
☀️
Afternoon
Carriage Road System — Eagle Lake Loop
★ 4.7John D. Rockefeller Jr. funded and personally supervised the construction of 45 miles of motor-free carriage roads between 1913 and 1940 — the roads are crushed stone, 16 feet wide, with 17 hand-built stone bridges. The Eagle Lake loop (6 miles, flat) is the most rewarding afternoon carriage road ride; bicycle rentals are available in Bar Harbor.
2:45 PM📍 See location
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Evening
Café This Way
★ 4.7A Bar Harbor restaurant in operation since 1994, serving the island's most creative dinner menu in a room covered with local art. The roasted beet salad, house-made pasta, and wood-grilled fish change seasonally; the wine list leans toward small European producers. The most-reserved table is the corner booth facing Mount Desert Street.
5:00 PM📍 See location
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Bar Harbor Inn or Harborside Hotel
Bar Harbor Inn on the harbor dates to 1887; Harborside Hotel has a pool above the water.
Day 2 — Blue Hill Peninsula, ME
Day 2 — Blue Hill Peninsula, ME
🚗 5 hr 55 min driving📍 5 stops
🌅
Morning
🚗
Drive
Bar Harbor, ME → Blue Hill, ME
50 min8:00 AM → 8:50 AM
Blue Hill Heritage Trust Trails
The Blue Hill Peninsula's network of land trust trails traverses granite headlands, blueberry barrens, and salt marshes that define the Downeast character — rockier, quieter, and more remote than Acadia's managed landscape. The Blue Hill Mountain Trail (2.5 miles RT, 940 feet) provides the same quality of coastal summit view with a fraction of the crowds.
8:50 AM📍 See location
🍽️
Lunch
Arborvine
★ 4.8A Blue Hill restaurant in a 1830s Cape house, serving Maine farm-and-sea cuisine with a wine list that has won Wine Spectator recognition every year since 2003. The lobster bisque, pan-seared halibut, and house-made desserts are the kitchen's anchors; the room is four dining rooms of the original house, each with a different character.
9:50 AM📍 See location
☀️
Afternoon
🚗
Drive
Blue Hill, ME → Caterpillar Hill Overlook
15 min12:00 PM → 12:15 PM
Caterpillar Hill Overlook
★ 5A roadside overlook on Route 175 between Sedgwick and Deer Isle that provides a view of Eggemoggin Reach and the Deer Isle-Stonington Bridge across one of the most beautiful stretches of the Maine coast — blue water, green islands, lobster boats, and the White Mountains in the far distance. The blueberry barrens in the foreground turn scarlet in September.
12:15 PM📍 See location
🚗
Drive
Caterpillar Hill Overlook → Deer Isle Granite Museum
20 min1:15 PM → 1:35 PM
Deer Isle Granite Museum
Deer Isle granite quarried here built the base of the Statue of Liberty, the plaza at Rockefeller Center, and the Kennedy Memorial in Washington. The museum in Stonington documents the quarrying era through photographs, tools, and a 15-foot operating model of the quarry at peak production in 1900, when 300 men worked the stone face.
1:35 PM📍 See location
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Evening
The Fisherman's Friend Restaurant
A Stonington institution on the working waterfront, The Fisherman's Friend serves freshly caught lobster, chowder, and fried seafood platters to island fishermen and visitors alike. Essential for a final Down East meal before the long drive south.
5:00 PM📍 See location
🚗
Drive
Stonington, ME → Boston, MA
4 hr 30 min6:00 PM → 10:30 PM
Return via Ellsworth, Bangor, and I-95 south.
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