Free Time Suggestions: Edgartown

If you're staying in Edgartown, you're in arguably the best spot on the island for a girls trip centered around food, shopping, strolling, and not needing to drive much. The downtown area is compact, charming, and highly walkable.

Leisurely Activities in Edgartown

Morning: Coffee + Harbor Walk

Start with coffee and pastries at:

  • Behind the Bookstore — waterfront seating overlooking the harbor.

  • Rosewater Market — great breakfast sandwiches and coffee.

Then wander:

  • Edgartown Harbor

  • The historic whaling captain homes along North Water Street

  • The lighthouse at Edgartown Lighthouse

Best Shopping Areas

Everything below is within a pleasant walk of downtown.

Main Street & North Water Street

Expect:

  • Coastal fashion boutiques

  • Vineyard-themed gifts

  • Jewelry stores

  • Art galleries

  • Home décor shops

Particularly fun stops:

  • Vineyard Vines (the brand's island roots are a fun stop)

  • Soft as a Grape

  • CB Stark Jewelers

Lunch Recommendations

Casual & Delicious

The Port Hunter

  • Seafood tacos

  • Lobster rolls

  • Great cocktails

19 Raw Oyster Bar

  • Oysters

  • Small plates

  • Rosé-friendly afternoon vibe

Among the Flowers Cafe

  • Outdoor garden seating

  • Salads and sandwiches

  • Excellent people-watching

Afternoon Activities (No Car Required)

1. Harbor Beach Time

Walk to:

  • Lighthouse Beach

It's ideal for:

  • Reading

  • Sunbathing

  • Picnic snacks

  • Quick swims

2. Bike Rental

Rent cruisers and explore:

  • Edgartown → Katama

  • Edgartown → South Beach

The island's bike paths are excellent.

3. Chappy Ferry Adventure

Take the tiny:

  • Chappaquiddick Ferry

It's a fun 5-minute crossing and feels like a mini excursion. Even a short ride over and back makes for a memorable afternoon.

Pre-Dinner Drinks

The Covington

Sophisticated cocktails and one of the island's more stylish atmospheres.

The Port Hunter

Lively bar scene with outdoor seating.

Atlantic Fish & Chophouse

Great harbor views at sunset.

Dinner Splurge Options

Detente

  • Romantic

  • Upscale

  • Excellent wine list

The Covington

  • Creative menu

  • Trendy without being overly formal

  • Great for a celebratory girls night

Atlantic Fish & Chophouse

  • Waterfront

  • Seafood-focused

  • Prime sunset location

One Evening Worth Leaving Edgartown For

Take a taxi or rideshare to:

  • Oak Bluffs

Reasons:

  • More nightlife

  • Live music

  • Ice cream shops

  • Walking around the colorful gingerbread cottages at Martha's Vineyard Camp Meeting Association Cottages