Maine Trip Mid-September

Question

Considering a trip to Maine for my Birthday mid-September. It will be my Wife and I, an early 60's couple that enjoys small towns with shopping and restaurants. Prefer accommodations close to the ocean with a view, no budget and are picky about staying somewhere clean, quiet, and semi-luxurious (LOL). Would enjoy scenic walks, but not all that adventurous. Expect we will have about 5 days in Maine and would prefer staying in one location or 2 at the most. Considering flying into Boston and renting a car or flying into Boston and taking the train to Portland.

My questions:

- Can we expect cooler temps mid-September? We have lived in Southern California most of our lives and recently migrated to Charlotte. Want to make sure we bring the proper clothing.

- Is Portland worth visiting for a day or two? We have enjoyed Boston numerous times, just not sure about Portland as a place to visit.

- Any small towns you would recommend with good accommodations, restaurants, and shopping?

This forum has been enormously helpful with planning, so I thank you in advance for your help.

Regards,

Dan

Answer

Mid-September is a wonderful time to visit Maine. The summer crowds have thinned, the fall foliage is beginning to show, and the weather is generally pleasant. You can expect cooler temperatures than what you might be used to in Southern California or even Charlotte. Daytime highs typically range from the mid-60s to low 70s Fahrenheit (18–23°C), while evenings can drop into the 50s (10–15°C). It’s wise to pack layers—light sweaters, a medium-weight jacket, and comfortable walking shoes are recommended, along with some rain protection just in case.

Portland is absolutely worth visiting, even if just for a day or two. It’s a charming coastal city with a vibrant food scene, historic Old Port district, and scenic waterfront. You can enjoy boutique shops, art galleries, and excellent restaurants—everything from fresh seafood to artisanal pastries. A day or two in Portland gives you a nice balance of city-like amenities without the scale of Boston.

For small towns with great accommodations, shopping, and restaurants, Maine has several excellent options. Since you prefer staying in one or two locations, you could consider combining a Portland stay with one or two nearby coastal towns:

Ogunquit: A small coastal town with beautiful beaches, scenic Marginal Way walking path, and an array of boutique shops and restaurants. There are several charming inns and small luxury hotels with ocean views.
Kennebunkport: Known for its picturesque harbor, high-end boutiques, art galleries, and seafood restaurants. There are luxury inns and oceanfront hotels that offer quiet, semi-luxurious stays.
Camden: Slightly farther north, this town offers a scenic harbor, hills for gentle walks, and a charming downtown with local shops and dining options. Accommodations include inns and boutique hotels overlooking the water.
Boothbay Harbor: Another charming coastal town with a harbor, boat tours, and a relaxed atmosphere. It’s great for scenic walks and has a selection of waterfront accommodations.

Given your preferences, a suggested itinerary could be:

Fly into Boston, rent a car, and drive to Portland (about 1.5–2 hours). Spend 1–2 nights exploring Portland, enjoying the Old Port, waterfront, and dining.
Drive north to a small coastal town like Ogunquit or Kennebunkport for the remainder of your trip (3 nights), staying in an oceanfront hotel or inn. Enjoy scenic walks, boutique shopping, and fine dining in a relaxed setting.

This combination provides a comfortable pace with minimal hotel changes while giving you a mix of city charm and small-town coastal beauty.

Additional tips:

Mid-September is off-peak, so you can often find excellent accommodations at reasonable rates.
Evenings can be chilly by the ocean, so a warm layer is essential for sunset walks or dining on patios.
If you love scenic drives, the stretch along Route 1 through southern coastal towns is beautiful and easy to navigate.

Overall, this trip would offer a mix of quiet luxury, coastal scenery, and charming towns for shopping and dining, with temperatures perfect for layered outfits and scenic strolls.