Westbrook Inn Bed & Breakfast September Newsletter 2026

You don't have to go far from Westbrook to find a full day of fall.

Here's where we'd send you.

• Bishop's Orchards, Guilford (about 20–25 minutes away) Their Fall Festival runs September 5 through November 1 — pick-your-own apples and pears, a pumpkin patch, a four-acre corn maze, wagon rides on weekends, and cider donuts that are worth the drive on their own.

• Essex & the Connecticut River Fifteen minutes up the shoreline gets you Essex Village, foliage along the river, and the Connecticut River Museum's Tree Swallow Sunset Cruises, running through September 23 — hundreds of thousands of swallows gathering over the water just before dark. It's one of those things you have to see once.

• Guilford for the Leaves Guilford just landed the #4 spot on Connecticut's list of best towns for fall foliage. Pair the Green with a stop at Hammonasset Beach — quieter now, better for walking, biking, and watching the sun go down over the water.

• Lyman Orchards, Middlefield (about 35–45 minutes) Worth the extra drive if you want to make a full day of it. Their corn maze opens September 5, and two weekends are worth circling: September 5–6 (Corn Maze & Cider Donut Festival, with live bluegrass and square dancing) and September 12–13 (Harvest Music Festival, live music and a beer garden). Halloween weekend brings the Brew Maze — flashlights, a corn maze, and Connecticut craft beer, adults only.

However you spend the day, come back to Westbrook for the evening. That part we can promise you'll love.

Fall on the Shoreline

Reserve Your Seat for Fall Tea at the Inn

Yes, we're already thinking past the leaves. The good tables go fast, so grab your date now.

September 3, 12 -1:30 pm 

(before the matinee showing of "Come from Away" at the Ivoryton Playhouse

October 6, 12 - 2 pm

Autumn Tea

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November 3, 12 - 2 pm

Victorian Afternoon Tea

December 1, 12 - 2 pm

Fireside Tea

There's a reason so many proposals happen here in October. The light does something different this time of year. It'sg olden on the water, gold in the trees. and it has a way of making people say the thing they came here to say.

Whether you're planning to pop the question on the beach at sunset or you're ready to elope with just the two of you and a good photographer, we'd love to be part of it.

A firelit room, a quiet porch, a table set for two, as much or as little fuss as you want.

If fall is the season, we're happy to help you plan it. Just reach out and tell us what you're picturing.

Proposal Packages Start at $350

Elopement Packages Start at $950

Say "YES" this Fall at the Inn

Live Music, Every Direction You Turn

• The Kate — always worth checking the calendar.

• Scotch Plains Tavern — for when you want music with your dinner, not instead of it.

• Coastline Brewing— good for the nights you didn't plan anything and that's fine too.
  

Our Favorite spots