Coastal Maine Itinerary

Maine Trip

August 1–8, 2026

Travelers: Michael & Diane Rental car available throughout

Trip Overview

Confirmed reservation Unbooked option Kate Rec Kate's recommendation
Saturday · August 1

Bangor to Stonington

Estimated drive: 1 hr 40–45 min · ~63 miles
WERU Community Radio Kate Rec
Listen while you settle in. weru.org
Sunday · August 2

Stonington and Deer Isle

Estimated local driving: 15–30 min between stops
Note: Do not schedule an Acadia day trip — it would add too much driving.
Monday · August 3

Stonington to Rockport through Belfast

Stonington → Belfast: 1 hr 35 min · ~59 mi  ·  Belfast → Rockport: 40–45 min · ~23 mi
Lunch & a walk in Belfast Kate Rec
Stop in Belfast on the way south.
Strawberry Hill Seaside Inn Confirmed · Lodging
Check in at 2:00 p.m. Relax at the inn or visit Camden Harbor.
📍 886 Commercial Street, Rockport, ME 04856 · strawberryhillseasideinn.com
Waterfront Restaurant Kate Rec Unbooked
Optional dinner.
📍 48 Bay View Street, Camden, ME 04843 · waterfrontcamden.com
Kate suggests visiting at an off-hour and sitting outside on the deck.
Tuesday · August 4

Camden and Camden Hills

From the Rockport inn: 20–25 min each way · ~8 miles
Camden Hills State Park Kate Rec
Choose one moderate hike.
📍 280 Belfast Road, Camden, ME 04843 · Trail conditions
Preferred hike: Maiden's Cliff. Kate Rec
Avoid the Mt. Battie trail. Kate Rec

Dinner options

1 · Waterfront Restaurant Kate Rec Unbooked
📍 48 Bay View Street, Camden, ME 04843 · waterfrontcamden.com
2 · Salt Wharf Kate Rec Unbooked
📍 3 Wayfarer Drive, Camden, ME 04843 · saltwharf.com
Wednesday · August 5

Rockport to Rockland

Estimated drive: 10–15 min · ~3 miles
Rockland Harbor Hotel Confirmed · Lodging
Check in after 4:00 p.m.
📍 520 Main Street, Rockland, ME 04841 · rocklandharborhotel.com
Sammy's Deluxe — Dinner Confirmed · Reservation
August 5 at 5:45 p.m. · Two guests.
📍 488 Main Street, Rockland, ME 04841 · Reservation on Tock
Primo — optional replacement Kate Rec Unbooked
Resy Notify is active from 5:00–7:30 p.m. Not confirmed — only if a table opens up.
📍 2 Main Street, Rockland, ME 04841 · primorestaurant.com
Thursday · August 6

Monhegan Island ferry option

Rockland → Port Clyde: 40–45 min · ~18 miles
Monhegan Island day trip Kate Rec Unbooked Option
Live availability was confirmed on July 23, but nothing has been booked. Friday is the weather fallback.
Total estimated price: $120.84 for two adults — round-trip ferry tickets, one day of parking and booking fees.

On the island

Bring hiking shoes, water, layers, sun protection and lunch or snacks.
Friday · August 7

Weather backup or flexible Midcoast day

If Thursday's weather prevents Monhegan: move the ferry option to Friday.

If Monhegan happens Thursday, choose one:

1 · Relax in Rockland or revisit Camden
Estimated Rockland-to-Camden drive: 20–25 min each way.
2 · Complete the Camden Hills hike
If Tuesday's weather prevented it.
3 · Damariscotta & River House Kate Rec Unbooked
Estimated drive: 50–55 min each way · ~27 miles.
📍 27 Main Street, Damariscotta, ME 04543 · riverhouseme.com
4 · Five Islands Lobster Co. Kate Rec Unbooked
Estimated drive: 1 hr 35–40 min each way · ~55 miles.
📍 1447 Five Islands Road, Georgetown, ME 04548 · fiveislandslobster.com
Kate recommends going early and avoiding Red's Eats.

Least-relaxed option — most driving

Saturday · August 8

Camp Kieve and flight home

Rockland → Camp Kieve: 55–60 min · ~28 mi  ·  Camp Kieve → Portland: 1 hr 40–50 min · ~63 mi
Camp Kieve Confirmed · Commitment
Camp commitment ends at 9:00 a.m.
📍 42 Kieve Road, Nobleboro, ME 04555 · kwe.org/kieve
Rental-car return — Alamo, Portland International Jetport Confirmed · Rental car
Return deadline: 2:00 p.m.
📍 1001 Westbrook Street, Portland, ME 04102
Flight home Confirmed · Flight
Departs Portland at 3:40 p.m. · Arrives Chicago Midway at 5:15 p.m. CDT.
Do not add another stop or formal lunch reservation that morning.

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