How to Enjoy the Best Fall Weekend Getaway in New England

Boothbay Harbor, Maine, is one of the best places to enjoy a fall weekend getaway in New England! During this time of year, the leaves burst into breathtaking displays of yellow, orange, and red and the air is refreshingly cool. On any given weekend during this season, Boothbay Harbor is full of exciting autumn activities. We’ve compiled a few of the best ways to make the most of the area’s beautiful weather and festive atmosphere on a weekend.

Just one fall weekend getaway in New England is not enough. There’s so much more to savor during Boothbay Harbor’s cooler months! Consider our suggestions in this post, but when you’re ready for more great ideas, consult our Things To Do in Boothbay Harbor Guide. 

How to Enjoy the Best Fall Weekend Getaway in New England

See Giant Pumpkins at the Damariscotta Pumpkinfest

What better way to kick off a fall weekend getaway in New England than witnessing enormous pumpkins? The Damariscotta Pumpkinfest is a popular fall festival held in Damariscotta, Maine, each Columbus Day Weekend. People flock to DRA’s Round Top Farm every year to honor fall’s arrival and learn a thing or two about agriculture. Over the course of two days, guests can attend a pumpkin parade, dramatic pumpkin drop, catapult demonstration, and pumpkin boat regatta. All of the Damariscotta Pumpkinfest events are free!

Taste Local Flavors at in Boothbay Harbor 

Boothbay Harbor is one of the best places in New England to see fall foliage. It’s also known for its local food scene! The vivid colors that surround guests are best enjoyed at one of the area’s seasonal food festivals or local restaurants.

Our sister properties offer Fall menus that are full of flavor with local produce, fresh seafood and meat, and unbeatable views from the restaurant:

The Pub at Newagen Seaside Inn

60 Newagen Colony Rd, Southport | 207 633 5242

One of the peninsula’s best-kept secrets, the Pub at Newagen Seaside Inn is away from the crowds and close to the sea. Open for lunch and dinner, enjoy an after-dinner drink in the red brick and wood-paneled pub or take your drink to the deck and sit at the outdoor fireplace. On Thursday and Sunday nights, you’ll also enjoy live, local music. Try the traditional lobster bake on Tuesday evening in July and August Open May-October for lunch and dinner. Check the website for hours.

the deck bar & grill at linekin bay resort

92 Wall Point Rd, Boothbay Harbor | 207 633 2494

Open for lunch and dinner daily May-October at the waterfront Deck Bar & Grill or in the cozy and casual dining room. Come by boat and park at the dock or call the resort’s tender to pick you up from a dedicated LBR mooring. Check the website for hours.


Or, choose to savor farm-fresh oysters at the Pemaquid Oyster Festival on Sunday, September 28th, 2019 from noon to dusk. The area’s breathtaking fall landscape will be in full view late September through October. 

Attend the Fall Foliage Festival

The Fall Foliage Festival in Boothbay Harbor is a prime way for locals and visitors alike to take full advantage of the area’s radiant foliage displays. Held every Columbus Day in the Boothbay Railway Village, this festive event celebrates both the changing of the seasons and local artisans who produce community goods year-round. At the event, expect live music, craft shows, delicious food, traditional autumn activities like pumpkin carving, and much more. Several exhibits will also be on display to guide visitors through Boothbay Harbor’s interesting history.

Get Cozy at the Russell House Bed & Breakfast

Planning a fall weekend getaway in New England? There’s no better place than The Russell House Bed & Breakfast to get cozy by a warm fire after a day of observing stunning autumn leaves! Located right in the center of town, our 8 unique guest rooms combine luxury and comfort and feature a queen or king bed, comfortable furnishings, private bathrooms, and hotel amenities. Two of our rooms even have a gas fireplace, perfect for those chillier nights!

Whether guests book in advance or embark on a last-minute weekend getaway in New England, they’ll want to return every year for our gorgeous autumn solstice and spacious accommodations.

Guest Room During a Fall Weekend Getaway in Maine
Be sure to check our availability while there’s still time to plan an autumn escape. There’s no better place to experience the harvest season, so book a stay with us today!