Maine 2024
A no-kids long weekend with Emily — Portland delivered far more than we expected, and a day trip upstate to the mountains gave us one of the more memorable hikes we’ve ever attempted.
Highlights
- Portland Nightlife - Don’t underestimate Portland. The downtown has a couple of streets closed to traffic that are packed with outstanding restaurants and some of the best people watching around. It has a real energy to it — vibrant, unpretentious, and genuinely fun.
- Lobster on the Dock - The waterfront lobster restaurants are an absolute must. Eating fresh lobster right on the dock with the harbor in front of you is exactly what a Maine trip should feel like. Don’t skip it.
- Tumbledown Mountain — Brook Trail - We drove upstate for a day hike on the Brook Trail at Tumbledown Mountain. We didn’t make the summit — it was a bit above our abilities — but that didn’t take anything away from it. The trail is rugged and beautiful, and the views along the way were stunning. A very memorable day.
- The Coastal Drive Home - On the way back we drove down the New Hampshire coastline toward Boston to catch our flight. It was a beautiful stretch of road — rocky shores, small seaside towns, and a perfect way to close out the trip.
- Portland Lighthouses - The coastline around Portland is dotted with lighthouses. Walking the shoreline and taking them in is one of those simple pleasures that sticks with you.
Tips
- Stay downtown Portland — you’ll want to be able to walk to everything; the restaurant and bar scene is concentrated and very walkable
- The restaurants on the wharf are a must — go for lunch or early dinner and eat right on the water
- Walk the coastline and find the lighthouses; there are more than you’d expect and each one is worth the stop
- Take at least one day to go upstate — the hiking is excellent and a completely different experience from the city
- If you fly in through Boston, the coastal drive up and back along the New Hampshire shore is well worth the scenic route